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Journal articles on the topic 'Hofmann reaction'

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Published: 28 September 2022

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1

Rane, Dhananjay S., and Man M. Sharma. "New strategies for the Hofmann reaction." Journal of Chemical Technology AND Biotechnology 59, no. 3 (March 1994): 271–77. http://dx.doi.org/10.1002/jctb.280590310.

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2

Martínez, Claudio, and Kilian Muñiz. "An Iodine-Catalyzed Hofmann-Löffler Reaction." Angewandte Chemie International Edition 54, no. 28 (May 28, 2015): 8287–91. http://dx.doi.org/10.1002/anie.201501122.

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3

Debnath, Pradip. "Recent Advances in the Hofmann Rearrangement and Its Application to Natural Product Synthesis." Current Organic Chemistry 23, no. 22 (January 8, 2020): 2402–35. http://dx.doi.org/10.2174/1385272823666191021115508.

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: C-N bond formation reactions are the most important transformations in (bio)organic chemistry because of the widespread occurrence of amines in pharmaceuticals, natural products, and biologically active compounds. The Hofmann rearrangement is a well-known method used for the preparation of primary amines from amides. But, the traditional version of the Hofmann rearrangement often gave relatively poor yields due to over-oxidation or due to the poor solubility of some amides in aqueous base, and created an enormous amount of waste products. Developments over the last two decades, in particular, have focused on refining both of these factors affecting the reaction. This review covers both the description of recent advances (2000-2019) in the Hofmann rearrangements and its applications in the synthesis of heterocycles, natural products and complex molecules of biological interest. It is revealed that organo-catalytic systems especially hypervalent iodine-based catalysts have been developed for the green and environmentally friendly conversion of carboxamides to primary amines and carbamates.

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4

Gao, Wenjing, Yameng Wan, Zhiguo Zhang, Hao Wu, Tongxin Liu, and Guisheng Zhang. "The Hofmann reaction involving annulation of o-(pyridin-2-yl)aryl amides selectively and rapidly leads to potential photocatalytically active 6H-pyrido[1,2-c]quinazolin-6-one derivatives." Green Chemistry 22, no. 22 (2020): 7955–61. http://dx.doi.org/10.1039/d0gc02777d.

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An intramolecular Hofmann reaction leads to diverse photocatalytically active 6H-pyrido[1,2-c] quinazolin-6-one derivatives with the advantages of mild reaction conditions, short reaction time, excellent yields, broad substrate scope and high FG tolerance.

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5

RANE, D. S., and M. M. SHARMA. "ChemInform Abstract: New Strategies for the Hofmann Reaction." ChemInform 25, no. 41 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199441082.

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6

Troev, K., and D. Max Roundhill. "HOFMANN ELIMINATION REACTION WITH PHOSPHORUS CONTAINING ALKYLAMMONIUM SALTS." Phosphorous and Sulfur and the Related Elements 37, no. 3-4 (June 1988): 243–45. http://dx.doi.org/10.1080/03086648808079044.

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7

Martinez, Claudio, and Kilian Muniz. "ChemInform Abstract: An Iodine-Catalyzed Hofmann-Loeffler Reaction." ChemInform 46, no. 45 (October 22, 2015): no. http://dx.doi.org/10.1002/chin.201545130.

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8

Sumi, Kenzo, Takao Ikariya, and Ryoji Noyori. "Efficient synthesis of optically active 2-amino-2'-diphenylphosphino-1,1'-binaphthyl and its derivatives." Canadian Journal of Chemistry 78, no. 6 (June 1, 2000): 697–703. http://dx.doi.org/10.1139/v99-248.

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Optically active 2-amino-2'-diphenylphosphino-1,1'-binaphthyls having various functional groups, such as amino, alkoxycarbonylamino, acylamino, mono- and dialkylamino, and sulfonylamino at C2 position were prepared. The key intermediate of the above aminophosphines was 2-carbamoyl-2'-diphenylphosphinyl-1,1'-binaphthyl synthesized from optically active 2-cyano-2'-diphenylphosphinyl-1,1'-binaphthyl. The transformation of the carbamoyl group to an amino group was effected by the Hofmann reaction.Key words: aminophosphine ligand, Hofmann reaction, optically active phosphine ligand.

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9

Xu, Qing, Huamei Xie, Er-Lei Zhang, Xiantao Ma, Jianhui Chen, Xiao-Chun Yu, and Huan Li. "Selective catalytic Hofmann N-alkylation of poor nucleophilic amines and amides with catalytic amounts of alkyl halides." Green Chemistry 18, no. 14 (2016): 3940–44. http://dx.doi.org/10.1039/c6gc00938g.

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A selective Hofmann N-alkylation reaction of amines/amides catalytic in alkyl halides is achieved by using alcohols as the alkylating reagents, affording mono- or di-alkylated amines/amides in high selectivities.

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10

Rao, M. L. Bhaskara, and Santi R. Palit. "Preparation of a Polyampholyte from Polyacrylonitrile by the Hofmann Reaction." Journal of Polymer Science Part C: Polymer Symposia 22, no. 2 (March 13, 2007): 587–90. http://dx.doi.org/10.1002/polc.5070220204.

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11

Khoroshunova, Yulia V., Denis A. Morozov, Andrey I. Taratayko, Sergey A. Dobrynin, Ilia V. Eltsov, Tatyana V. Rybalova, Yulia S. Sotnikova, Dmitriy N. Polovyanenko, Nargiz B. Asanbaeva, and Igor A. Kirilyuk. "The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4." Molecules 26, no. 19 (October 2, 2021): 6000. http://dx.doi.org/10.3390/molecules26196000.

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Activation of a hydroxyl group towards nucleophilic substitution via reaction with methanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to various functional derivatives. The reactions of (5R(S),6R(S))-1-X-6-(hydroxymethyl)-2,2-dimethyl- 1-azaspiro[4.4]nonanes 1a–d (X = O·; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahydro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocyclopenta[c]azepines (4–6) (for X = OBn, OBz), or perhydro-cyclopenta[2,3]azeto[1,2-a]pyrrol (3) (for X = H) derivatives. Alkylation of the latter with MeI with subsequent Hofmann elimination afforded 2,3,3-trimethyl-1,2,3,4,5,7,8,8a-octahydrocyclopenta[c]azepine with 56% yield.

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12

Del Castillo, Estefanía, and Kilian Muñiz. "Enantioselective Synthesis of Nicotine via an Iodine-Mediated Hofmann–Löffler Reaction." Organic Letters 21, no. 3 (January 23, 2019): 705–8. http://dx.doi.org/10.1021/acs.orglett.8b03909.

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13

Matsumura, Yoshihiro, Yuki Satoh, Kimihiro Shirai, Osamu Onomura, and Toshihide Maki. "New reaction conditions using trifluoroethanol for the E-I Hofmann rearrangement." Journal of the Chemical Society, Perkin Transactions 1, no. 15 (1999): 2057–60. http://dx.doi.org/10.1039/a904126e.

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14

Banert, Klaus, Manuel Heck, Andreas Ihle, Erik Michael, and Richard Weber. "Record-Breaking Steric Crowding in Trialkylamines Prepared by Oxidative Ring Opening." Synthesis 52, no. 24 (October 5, 2020): 3801–10. http://dx.doi.org/10.1055/s-0040-1707294.

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AbstractEpoxidation of olefinic heterocyclic amines and subsequent acid-catalyzed hydrolysis or alternatively the direct dihydroxylation with the help of osmium tetroxide led to diols, which underwent ring cleavage in the presence of lead tetraacetate to give 3-isopropyl-2,2,4,4-tetramethyl-3-azahexanedial and 3-tert-butyl-2,2,4,4-tetramethyl-3-azapentanedial. Whereas the former dialdehyde is a highly unstable model compound because of a rapid intramolecular aldol reaction, the latter product proves to be isolable at room temperature. Furthermore, this compound is the first open-chain tri-tert-alkylamine establishing in a new record of steric crowding in tertiary amines. Strong tendencies to a Hofmann-like elimination reaction or to ring-closing reactions were observed when the aldehyde units of 3-tert-butyl-2,2,4,4-tetramethyl-3-azapentanedial were transformed into other functionalities, since both types of reactions led to a significantly decrease of the steric stress.

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15

Bain, Cheryl D., Julia M. Bayne, D. Scott Bohle, Ian S. Butler, and Joël Poisson. "Synthesis of reduction-sensitive 1,1-diarylhydrazines from 1,1-diarylamines." Canadian Journal of Chemistry 92, no. 9 (September 2014): 904–12. http://dx.doi.org/10.1139/cjc-2014-0132.

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1-(2-Nitrophenyl)-1-phenylamine and methyl 4-((2-nitrophenyl)amino)benzoate have been transformed into their corresponding urea derivatives through the action of chlorosulfonyl isocyanate. The initial sulfimidate product from the former reaction has sufficient stability so that it can be isolated and characterized as its disodium salt, and this, as well as three other subsequent products, have been characterized by X-ray diffraction. The corresponding intermediary urea was converted into its hydrazine derivative via a Hofmann rearrangement under oxidative conditions. Density functional theory has been used to examine the nature of the intermediates and transition states for the Hofmann rearrangement. There is little theoretical indication for a cyclic aziridinonium intermediate and the transition state between the urea and the isocyanate corresponds to a reactant-like rotation of the planar singlet nitrene before migration and formation of the new N−N bond.

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16

Zhang, Jiayu, and Mónica H. Pérez-Temprano. "Intramolecular C(sp3)–H Bond Amination Strategies for the Synthesis of Saturated N-containing Heterocycles." CHIMIA International Journal for Chemistry 74, no. 11 (November 25, 2020): 895–903. http://dx.doi.org/10.2533/chimia.2020.895.

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The selective functionalization of C(sp3)–H bonds via intramolecular amination reactions represents a very attractive strategy for the construction of saturated N-containing heterocycles (SNHets). Over the past de- cades, the chemical community has devoted its efforts towards expanding the synthetic toolbox with the aim of facilitating access to these key fragments in a controllable, reproducible and efficient manner. This review covers selected examples of the most recent advances in intramolecular C(sp3)–N bond-forming reactions by three main approaches: (1) the Hofmann-Löffler-Freytag (HLF) reaction; (2) transition-metal-catalyzed nitrene C(sp3)–H inser- tion; and (3) transition-metal-catalyzed ligand-assisted C(sp3)–N bond-forming reactions via a reductive elimination step. We will discuss reactivity, selectivity and the major mechanistic insights into these transformations.

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17

Rahman, Aziz-Ur, and M. O. Farooq. "Hofmann rearrangement of diphenylacetamide & ββ-diphenylpropionamide. Schiff's base as a new by-product of the Hofmann reaction. Benzhydryl-amine from diphenylacethydroxamic acid." Recueil des Travaux Chimiques des Pays-Bas 73, no. 5 (September 2, 2010): 423–30. http://dx.doi.org/10.1002/recl.19540730511.

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18

Xiaojie, Xu, Yao Zhengui, Ye Xiulin, Tang Youqi, Fu Heng, and Qian Minxie. "THE CONFORMATIONAL ANALYSIS AND REACTION MECHANISM FOR HOFMANN ELIMINATION OF QUATERNARY AMMONIUM HYDROXIDES." Acta Physico-Chimica Sinica 5, no. 04 (1989): 398–402. http://dx.doi.org/10.3866/pku.whxb19890405.

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19

Mandel, Sarah M., and Matthew S. Platz. "Reaction of Benzoylnitrene with Anions: Formation of an Intermediate in the Hofmann Rearrangement." Organic Letters 7, no. 24 (November 2005): 5385–87. http://dx.doi.org/10.1021/ol051985y.

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20

Zhang, Duo, Han Wang, Hanchao Cheng, José G. Hernández, and Carsten Bolm. "An Iodine-Mediated Hofmann-Löffler-Freytag Reaction of Sulfoximines Leading to Dihydroisothiazole Oxides." Advanced Synthesis & Catalysis 359, no. 24 (October 16, 2017): 4274–77. http://dx.doi.org/10.1002/adsc.201701178.

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21

Matsumura, Yoshihiro, Yuki Satoh, Kimihiro Shirai, Osamu Onomura, and Toshihide Maki. "ChemInform Abstract: New Reaction Conditions Using Trifluoroethanol for the E-I Hofmann Rearrangement." ChemInform 30, no. 44 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199944220.

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22

Sep�lveda-Arques, J., Eugenia Gonzalez Rosende, Dolores Perona Marmol, Elena Zaballos Garc�a, B. Yruretagoyena, and J. Ezquerra. "Unusual Hofmann elimination at low temperature. Reaction of 3-hydroxymethylpyrrolidines withp-toluensulfonyl chloride." Monatshefte f�r Chemie Chemical Monthly 124, no. 3 (March 1993): 323–25. http://dx.doi.org/10.1007/bf00810590.

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23

Krunic, Mihajlo, Ivana Jevtic, Jelena Penjisevic, and Sladjana Kostic-Rajacic. "Synthetic route towards 1,2,3,4-tetrahydroquinoxaline/piperidine combined tricyclic ring system." Journal of the Serbian Chemical Society, no. 00 (2021): 68. http://dx.doi.org/10.2298/jsc210416068k.

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The synthetic route toward novel tricyclic, nitrogen-containing system is disclosed. Three novel compounds possessing structural features of 1,2,3,4-tetrahydroquinoxaline and decahydropyrido[3,4-b]pyrazine are synthesized starting from readily available precursors in six or seven steps, of which the last three or four steps respectfully are diastereoselective. Key reaction steps include N-acylation, Hofmann rearrangement and ring-closing Buchwald-Hartwig reaction. Compounds trans-8, cis-12 and trans-12 are synthesized in order to prove that this novel, tricyclic system can be functionalized with various groups. Synthetic significance of this heterocyclic system lies in the possibility for the orthogonal functionalization of three different amino groups, allowing fine structural tuning.

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24

Beltrame, Paolo, Pier Luigi Beltrame, Paolo Carniti, Pietro Delogu, Carlo Pina, and Giovanni Zuretti. "Synthesis of [2.2]paracyclophane via Hofmann elimination: a kinetic study of the homogeneous reaction." Industrial & Engineering Chemistry Research 28, no. 8 (August 1989): 1125–30. http://dx.doi.org/10.1021/ie00092a002.

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25

Tanaka, Hiroo, and Lars Ödberg. "Preparation of cationic polyacrylamides by a modified Hofmann reaction: Fluorescent labeling of cationic polyacrylamides." Journal of Polymer Science Part A: Polymer Chemistry 27, no. 13 (December 1989): 4329–39. http://dx.doi.org/10.1002/pola.1989.080271310.

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26

Tyukhteneva, Z. I., and L. A. Badovskaya. "Lactonization of N-Benzyl-3-benzylamino-4-hydroxybutyramide under the Hofmann-Loffler Reaction Conditions." Russian Journal of Organic Chemistry 41, no. 6 (June 2005): 937. http://dx.doi.org/10.1007/s11178-005-0270-3.

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27

Duhamel, Thomas, Mario D. Martínez, Ioanna K. Sideri, and Kilian Muñiz. "1,3-Diamine Formation from an Interrupted Hofmann–Löffler Reaction: Iodine Catalyst Turnover through Ritter-Type Amination." ACS Catalysis 9, no. 9 (July 29, 2019): 7741–45. http://dx.doi.org/10.1021/acscatal.9b01566.

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28

Banert, Klaus, Manfred Hagedorn, Manuel Heck, Raphael Hertel, Andreas Ihle, Ioana Müller, Tom Pester, Tharallah Shoker, and Paul R. Rablen. "Synthesis of Trialkylamines with Extreme Steric Hindrance and Their Decay by a Hofmann-like Elimination Reaction." Journal of Organic Chemistry 85, no. 21 (October 28, 2020): 13630–43. http://dx.doi.org/10.1021/acs.joc.0c01790.

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29

SEPULVEDA-ARQUES, J., E. GONZALEZ ROSENDE, D. PERONA MARMOL, E. ZABALLOS GARCIA, B. YRURETAGOYENA, and J. EZQUERRA. "ChemInform Abstract: Unusual Hofmann Elimination at Low Temperature. Reaction of 3- Hydroxymethylpyrrolidines with p-Toluenesulfonyl Chloride." ChemInform 24, no. 27 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199327090.

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30

Mocci, Rita, Sergio Murgia, Lidia De Luca, Evelina Colacino, Francesco Delogu, and Andrea Porcheddu. "Ball-milling and cheap reagents breathe green life into the one hundred-year-old Hofmann reaction." Organic Chemistry Frontiers 5, no. 4 (2018): 531–38. http://dx.doi.org/10.1039/c7qo01006k.

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31

Wang, Long-Fei, Wei-Man Zhuang, Guo-Zhang Huang, Yan-Cong Chen, Jiang-Zhen Qiu, Zhao-Ping Ni, and Ming-Liang Tong. "Spin-crossover modulation via single-crystal to single-crystal photochemical [2 + 2] reaction in Hofmann-type frameworks." Chemical Science 10, no. 32 (2019): 7496–502. http://dx.doi.org/10.1039/c9sc02274k.

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Spin-crossover (SCO) system integrated with photochemical [2 + 2] reaction is firstly reported. The dimerization of azastilbene ligands dramatically modulated SCO properties, providing a new strategy for exploiting photo-responsive SCO materials.

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32

MORITA, KOSUKE. "SUPERHEAVY RESEARCH AT RIKEN." International Journal of Modern Physics E 18, no. 10 (November 2009): 2175–78. http://dx.doi.org/10.1142/s0218301309014500.

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At RIKEN (The Institute of Physical and Chemical Research) in Japan, we have performed experiments to study the productions and decays of the heaviest elements produced by one neutron emission channels of 208 Pb and 209 Bi based heavy-ion induced fusion reactions. A gas-filled type recoil separator has been used for collecting evaporation residues of the reactions separating them from high intensity beam particles. The reactions studied were 208 Pb (58 Fe , n )265 Hs , 208 Pb (64 Ni , n ) 271 Ds , 209 Bi (64 Ni , n ) 272 Rg , 208 Pb (70 Zn , n ) 277112, and 209 Bi (70 Zn , n ) 278113. In studies of the first four reactions we have provided the independent confirmations of the productions and their decays of the isotopes, 265 Hs , 271 Ds , 272 Rg , and 277112, as well as the decay properties of their decay daughters, previously studied by Hofmann et al., a group of Gesellschaft für Schwerionenforschung (GSI), Germany. In the last reaction, we observed two decay chains originated from the isotope 278113, assigned firstly by generic correlation of the alpha decay chains connected into the previously known decay of 266 Bh and 262 Db via previously unknown alpha decays of 278113, 274 Rg and 270 Mt .

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33

de Lima, Juliana A., Lays B. Fitaroni, Daniel VA Chiaretti, Manuela LQA Kaneko, and Sandra A. Cruz. "Degradation process of low molar mass poly(ethylene terephthalate)/organically modified montmorillonite nanocomposites." Journal of Thermoplastic Composite Materials 30, no. 4 (September 28, 2016): 504–20. http://dx.doi.org/10.1177/0892705715604678.

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The aim of this work is to investigate the degradation of low molar mass poly(ethylene terephthalate) (PET)/organically modified montmorillonite (OMMT) clay nanocomposites prepared by melt processing. The rheological behavior in combination with transmission electron microscopic images suggests an intercalation and therefore a percolating network. Furthermore, the results indicate that the increase of organoclay content caused a degradation of PET during processing of PET/OMMT nanocomposites, once it was observed the PET molar mass decreases. The effect mentioned could be attributed to an increase of Brønsted acidic sites on the platelet surface, which is produced by the Hofmann elimination reaction of ammonium, and also the presence of residual metal compounds on clay surface might possibly favored the polymer matrix degradation process.

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34

Hashimoto, Shizunobu, and Takayuki Yamashita. "Synthesis of Linear Poly(1-Benzyltrimethyleneimine) by the Hofmann Reaction of Poly(1-Cyanoethyltrimethyleneimine) Quaternized with Benzylbromide." Journal of Macromolecular Science: Part A - Chemistry 28, no. 5-6 (May 1991): 475–86. http://dx.doi.org/10.1080/00222339108052101.

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35

Huo, Jia-Min, Ying Wang, Jie Meng, Xin-Yi Zhao, Quan-Guo Zhai, Yu-Cheng Jiang, Man-Cheng Hu, Shu-Ni Li, and Yu Chen. "π⋯π interaction directed 2D FeNi-LDH nanosheets from 2D Hofmann-MOFs for the oxygen evolution reaction." Journal of Materials Chemistry A 10, no. 4 (2022): 1815–20. http://dx.doi.org/10.1039/d1ta09921c.

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A two-dimensional (2D) MOFs transformation strategy was introduced to synthesize FeNi layered double hydroxides (FeNi LDHs) in NaBH4 solution, which show excellent OER catalytic activity in alkaline media.

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36

Jackson, Catherine M. "Synthetical Experiments and Alkaloid Analogues." Historical Studies in the Natural Sciences 44, no. 4 (November 2012): 319–63. http://dx.doi.org/10.1525/hsns.2014.44.4.319.

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This essay provides the first historical account of the origins of synthetic organic chemistry, one of the most powerful and productive of late nineteenth-century sciences. It builds on a revised understanding of the program of organic analysis instituted in the early 1830s by Justus Liebig, showing why and how Liebig guided his students August Wilhelm Hofmann and James Sheridan Muspratt in the introduction of synthesis to organic chemistry in early 1840s Giessen. What Muspratt and Hofmann called “synthetical experiments” became Hofmann’s main investigative method, but they did not enable the artificial laboratory production of specified target substances. Instead, synthetical experiments increased chemical understanding of reactions and their products. When applied to aniline, Hofmann’s model for natural alkaloids, they produced the array of artificial organic bases underpinning Hofmann’s major theoretical innovation, the ammonia type. Despite his reliance on artificial bases, this essay shows that Hofmann’s primary and enduring scientific goal was to understand the natural alkaloids. By revealing the essential stabilizing and progressive role of chemists’ daily work at a time when theory was uncertain and contested, it contributes to ongoing studies of science as practice.

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37

Chan, Kwai S., Michael A. Miller, Carol Ellis-Terrell, and Candace K. Chan. "Synthesis and Characterization of Empty Silicon Clathrates for Anode Applications in Li-ion Batteries." MRS Advances 1, no. 45 (2016): 3043–48. http://dx.doi.org/10.1557/adv.2016.434.

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ABSTRACTSeveral processing methods were developed and evaluated for synthesizing empty silicon clathrates. A solution synthesis method based on the Hofmann-elimination oxidation reaction was successfully utilized to produce 20 mg of empty Si46. Half-cells using the Si46 electrodes were successfully cycled for 1000 cycles at rate of 5.3C. The capacity of the Si46 electrode in long-term tests was 675 mAh/g at the 4th cycle, but increased to 809 mAh/g at 50 cycles. The corresponding Coulombic efficiency was better than 99%. The capacity dropped from 809 to 553 mAh/g after 1000 cycles while maintaining a 99% Coulombic efficiency. In comparison, a Ba8Al8Si38 electrode could be cycled for about 200 cycles with a lower capacity and Coulombic efficiency. Potential applications of empty silicon clathrates as anode materials in Li-ion batteries are discussed.

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38

Zhao, Hong Chi, Qi Li, Wen Yu Xu, and Fan Huang. "Study on Synthesis and Thermal Property of Polyvinylamine." Advanced Materials Research 150-151 (October 2010): 1500–1503. http://dx.doi.org/10.4028/www.scientific.net/amr.150-151.1500.

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Polyvinylamine (PVAm) and polyvinylamine chloride (PVAm•HCl) were synthesized by Hofmann degradation of polyacrylamide (PAM). The reaction condition is gentle and the operation is safe, simple and economical so that it is a good reaction method. The chemical structures and thermal properties of the polymers were studied by Fourier transform infrared spectrometer (FTIR), nuclear magnetic resonance spectrometer (NMR), X-ray diffractmeter (XRD) and thermogravimetric analyzer (TGA). Synthesis of PVAm•HCl was confirmed by the intensities of the characteristic peak of -CONH2 decreased and the appearance of a new absorption peak at 1530cm-1 (due to N-H bond of -NH3+ ) in the FTIR spectrum, the appearance of the characteristic absorption peaks of carbon atoms in the 13C NMR spectrum, the appearance of chemical shift assignments of proton in 1H NMR spectrum and the appearance of characteristic dispersing diffraction peak between 22.5° to 25.2° in the XRD spectrum, respectively. PAM had three decomposing stages, but PVAm•HCl had two decomposing stages. TG curve of PAM and PVAm•HCl showed that the initial decomposition temperature were 190oC and 140oC, respectively. The thermal stability of PVAm•HCl was poorer than that of PAM.

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39

Leis, Hans Jörg, and Helmut Gleispach. "Characterization of the antidiarrhoeal loperamide by gas chromatography-mass spectrometry and application of the Hofmann degradation and Cope elimination reaction." Journal of Chromatography B: Biomedical Sciences and Applications 494 (January 1989): 324–30. http://dx.doi.org/10.1016/s0378-4347(00)82683-3.

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40

Zagulyaeva, Aleksandra A., Christopher T. Banek, Mekhman S. Yusubov, and Viktor V. Zhdankin. "Hofmann Rearrangement of Carboxamides Mediated by Hypervalent Iodine Species Generated in Situ from Iodobenzene and Oxone: Reaction Scope and Limitations." Organic Letters 12, no. 20 (October 15, 2010): 4644–47. http://dx.doi.org/10.1021/ol101993q.

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41

Lai, Yee-Hing, and Hong-Leng Eu. "Novel formation of 4-methylthiopyrene in a Hofmann elimination reaction directed toward the synthesis of 17,19-dioxa[2.2.3](1,2,3)cyclophanediene." Journal of the Chemical Society, Perkin Transactions 1, no. 2 (1993): 233. http://dx.doi.org/10.1039/p19930000233.

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42

Vasudevan, Anita, and Gerald F. Koser. "Direct conversion of long-chain carboxamides to alkylammonium tosylates with hydroxy(tosyloxy)iodobenzene, a notable improvement over the classical Hofmann reaction." Journal of Organic Chemistry 53, no. 21 (October 1988): 5158–60. http://dx.doi.org/10.1021/jo00256a051.

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43

LAI, Y. H., and H. L. EU. "ChemInform Abstract: Novel Formation of 4-Methylthiopyrene in a Hofmann Elimination Reaction Directed Toward the Synthesis of 17,19-Dioxa(2.2.3)(1,2,3)cyclophanediene." ChemInform 24, no. 18 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199318189.

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Zagulyaeva, Aleksandra A., Christopher T. Banek, Mekhman S. Yusubov, and Viktor V. Zhdankin. "ChemInform Abstract: Hofmann Rearrangement of Carboxamides Mediated by Hypervalent Iodine Species Generated in situ from Iodobenzene and Oxone: Reaction Scope and Limitations." ChemInform 42, no. 7 (January 20, 2011): no. http://dx.doi.org/10.1002/chin.201107044.

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Santy, Lorraine C., and Guido Guidotti. "Expression of a single gene produces both forms of skeletal muscle cyclic nucleotide-gated channels." American Journal of Physiology-Endocrinology and Metabolism 273, no. 6 (December 1, 1997): E1140—E1148. http://dx.doi.org/10.1152/ajpendo.1997.273.6.e1140.

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Cyclic nucleotide-gated cation channels in skeletal muscle are responsible for insulin-activated sodium entry into this tissue (J. E. M. McGeoch and G. Guidotti. J. Biol. Chem. 267: 832–841, 1992). These channels have previously been isolated from rabbit skeletal muscle by 8-bromoguanosine 3′,5′-cyclic monophosphate (8-BrcGMP) affinity chromatography, which separates them into two populations differing in nucleotide affinity [L. C. Santy and G. Guidotti. Am. J. Physiol. 271 ( Endocrinol. Metab. 34): E1051-E1060, 1996]. In this study, a polymerase chain reaction approach was used to identify skeletal muscle cyclic nucleotide-gated channel cDNAs. Rabbit skeletal muscle expresses the same cyclic nucleotide-gated channel as rabbit aorta (M. Biel, W. Altenhofen, R. Hullin, J. Ludwig, M. Freichel, V. Flockerzi, N. Dascal, U. B. Kaupp, and F. Hofmann. FEBS Lett. 329: 134–138, 1993). The entire cDNA for this gene was cloned from rabbit skeletal muscle and an antiserum to this protein produced. Expression of this cDNA produces a 63-kDa protein with cyclic nucleotide-gated channel activity. A similarly sized immunoreactive protein is present in sarcolemma. Purification of the expressed channels reveals that this single gene produces both native skeletal muscle channel populations.

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Li, Baibin, Jingwen Yuan, Xuebei Ye, Rui Zhang, Jiacheng Li, Yu Wang, Jiana Hu, and Dewen Dong. "PIFA-Mediated Tandem Hofmann-Type Rearrangement and Cyclization Reaction of α-Acyl-β-aminoacrylamides: Access to Polysubstituted Oxazol-2(3H)-ones." Journal of Organic Chemistry 86, no. 24 (December 7, 2021): 17944–54. http://dx.doi.org/10.1021/acs.joc.1c02276.

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Davies, Julian A., and Cassandra T. Eagle. "Electrochemical generation and reactivity of bis(triethylphosphine)platinum(O): formation of a platinum hydride via a Hofmann elimination reaction with the tetra-n-butylammonium cation." Organometallics 5, no. 10 (October 1986): 2149–51. http://dx.doi.org/10.1021/om00141a037.

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Eubanks, John R. I., Leslie B. Sims, and Arthur Fry. "Carbon isotope effect studies of the mechanism of the Hofmann elimination reaction of para-substituted (2-phenylethyl-1-14C)- and (2-phenylethyl-2-14C)-trimethylammonium bromides." Journal of the American Chemical Society 113, no. 23 (November 1991): 8821–29. http://dx.doi.org/10.1021/ja00023a034.

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Lechel, Tilman, Gabriel Podolan, Boris Brusilowskij, Christoph A. Schalley, and Hans-Ulrich Reissig. "Unexpected One-Step Formation of Iodo[1,3]dioxolo[4,5-c]pyridine Derivatives by a Hofmann-Löffler-Freytag Reaction: Studies on the Synthesis of a Pyridine-Containing Macrocycle." European Journal of Organic Chemistry 2012, no. 29 (September 7, 2012): 5685–92. http://dx.doi.org/10.1002/ejoc.201200564.

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Brauer, David J., Jörg Fischer, Stefan Kucken, Klaus P. Langhans, Othmar Stelzer, and Norbert Weferling. "Wasserlösliche Phosphane, III [1]. Wasserlösliche primäre Phosphane mit Ammoniumgruppierungen NR2R' in der Seitenkette -donorfunktionalisierte Amphiphile / Water-Soluble Phosphanes, III [1]. Water-Soluble Primary Phosphanes with Ammonium Groups NR2R' in the Side Chain -Donor-Functionalized Amphiphiles." Zeitschrift für Naturforschung B 49, no. 11 (November 1, 1994): 1511–24. http://dx.doi.org/10.1515/znb-1994-1111.

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Primary and secondary aminoalkylphosphanes R2N-(CH2)m-PH2 (R2 = Me2, nBu2, C5H10, C4H8O, 2-(1-Methyl-2-pyrrolidinyl); m = 2, 3, 6, 10, 11; 1-6) or [R2N-(CH2)m]2PH (7, R2 = C5H10; m = 2) are accessible by aminoalkylation of PH3 with ω̃ -chloroalkylamines R2N-(CH2)m-Cl in the superbasic medium DMSO/KOH (DMSO = dimethylsulfoxide). By selective N-quaternization of 1, 2, 4-6 with R'I (R' = Me, CnH2n+1; n = 6-8, 12, 16, 18) in the two-phase system CH2Cl2/H2O novel primary phosphanes [R'R2N-(CH2)m-PH2]+I- (11-16f) with quaternary ammonium groups in the alkyl side chain are obtained. The water solubility of 11-16f decreases with increasing chain length (n) of R′ 11 (R = R' = Me; m = 2) shows a trans conformation at the C2H4 bridge according to an X-ray structural analysis. Protonation of 1, 2, 4, 5 with HCl affords the water-soluble hydrochlorides [HR2N-(CH2)m-PH2]+Cl- (19-22). The cationic primary phosphanes 11-16f are stable towards oxygen. By oxidation of 11 with one or two equivalents of H2O2 the primary phosphane oxide [Me3N-(CH2)2-P(O)H2]+I- (23) or the phosphonous acid [Me3N-(CH2)2- P(O)(OH)H]+I- (23a) are formed. Hofmann degradation of 11 or 16c with KOH yields phosphirane in good yields. Reaction of 1, 2, 4-6 (L) with Fe2(CO)9 at ambient temperature yields stable complexes (CO)4FeL (26-30). Under more rigorous conditions Fe3 clusters (31, 32) with free R2N groups are obtained.

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