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Journal articles on the topic 'Ketenimine'

Author: Grafiati

Published: 18 May 2024

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1

Baradarani, M., RH Prager, and K. Schafer. "The Chemistry of 5-Oxodihydroisoxazoles. XV. Reaction of Derived Ketenimines With Enamines and Enolates." Australian Journal of Chemistry 49, no. 8 (1996): 911. http://dx.doi.org/10.1071/ch9960911.

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Reaction of 2-heterocyclisoxazol-5(2H)-ones with bases leads to the formation of ketenimines, which react with nucleophiles in competition with intramolecular reactions. Such reactions in the presence of enamines, enamine anions or enolates are reported. Enamines undergo addition through carbon and nitrogen to the ketenimine in competition with direct addition-elimination to the isoxazolone. Enolates of imines or ketones add to the ketenimine to give a mixture of products: only the reaction with the enolate of cyclohexanone is sufficiently specific to provide a useful new synthetic procedure.

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2

Ang, KH, RH Prager, and CM Williams. "The Chemistry of 5-Oxodihydroisoxazoles. XII. Trapping of Derived Ketenimines With Lithium Amides and Alkyllithiums." Australian Journal of Chemistry 48, no. 1 (1995): 55. http://dx.doi.org/10.1071/ch9950055.

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Isoxazolones unsubstituted at C3 react with lithium amides or alkyllithiums to give ketenimines . The presence of an ethoxycarbonyl group at C4 allows capture of this species by addition of a second equivalent of the lithiated species to give enolates which can be alkylated in situ. The presence of a phenyl group at C4 gives a ketenimine which reacts intramolecularly in the presence of lithium amides, whereas alkyllithiums undergo addition in synthetically useful processes.

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3

Yavari, Issa, Farough Nasiri, Hoorieh Djahaniani, and Hamid R. Bijanzadeh. "Synthesis and Dynamic NMR Study of Fluorinated Dialkyl 2-[(tert-butylimino)-methylene]-3-[(2-alkoxy-2-oxoacetyl)-2-fluoroanilino]-succinates." Journal of Chemical Research 2005, no. 8 (August 2005): 537–39. http://dx.doi.org/10.3184/030823405774663372.

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The 1:1 adduct produced in the reaction between tert-butyl isocyanide and dialkyl acetylenedicarboxylates was trapped by alkyl 2-fluoro-anilino-2-oxo-acetates or ethyl 2-oxo-2-(trifluoromethylanilino)-acetate to produce functionalised ketenimines in good yields. Dynamic NMR effects were observed in the 1H NMR spectra of these compounds as a result of restricted rotation around the single bond linking the aryl group to the ketenimine system. The free energy of activation (ΔG≠) for this process is 64.9–66.5 kJ mol−1.

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4

Alajarín, Mateo, Baltasar Bonillo, Pilar Sánchez-Andrada, Ángel Vidal, and Delia Bautista. "Intramolecular Ketenimine−Ketenimine [2 + 2] and [4 + 2] Cycloadditions†." Journal of Organic Chemistry 72, no. 15 (July 2007): 5863–66. http://dx.doi.org/10.1021/jo0704661.

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5

He, Wenxing, Xiaojun Tan, Nana Wang, and Hong Zhang. "Theoretical study on the mechanism of the cycloaddition reaction between ketenimine and hydrogen cyanide." Journal of the Serbian Chemical Society 81, no. 2 (2016): 187–95. http://dx.doi.org/10.2298/jsc150504091h.

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The cycloaddition reaction mechanism between interstellar molecules ketenimine and HCN has been investigated employing the second-order M?ller-Plesset perturbation theory (MP2) method in order to better understand the reactivity of nitrogenous cumulene ketenimine with carbon-nitrogen triple bond compound HCN. Geometry optimizations and vibrational analyses have been performed for the stationary points on the potential energy surfaces of the system. The calculated results show that it can be produced the five-membered cyclic carbene intermediates through pericyclic reaction processes between ketenimine and HCN. Through the following H-transfer processes, carbene intermediates can isomerize to the pyrazole and imidazole compounds, respectively. The present study is helpful to understand the formation of prebiotic species in interstellar space.

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6

Brown, RFC, KJ Coulston, and FW Eastwood. "Intramolecular Trapping of a Ketenimine Carbene Formed on Flash Vacuum Pyrolysis of 3-Phenylimino-3H-indazole and 3-Phenyliminoisobenzofuran-1-one." Australian Journal of Chemistry 47, no. 1 (1994): 47. http://dx.doi.org/10.1071/ch9940047.

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Flash vacuum pyrolysis of 3-phenylimino-3H-indazole yielded biphenylene , benzonitrile and, by loss of dinitrogen followed by intramolecular trapping of a ketenimine carbene intermediate, the isomers fluorenimine , phenanthridine and 2-phenylbenzonitrile.Pyrolysis of 3-phenyliminoisobenzofuran-1-one gave the same five products together with N- phenylphthalimide . It is proposed that the same ketenimine carbene intermediate is involved in the two reactions. Pyrolysis of 3-o-tolylimino- and 3-benzylimino-isobenzofuran-1-one led to fragmentation without intramolecular trapping. Pyrolysis of 3-t-butyliminoisobenzofuran-1-one gave o-cyanobenzoic acid.

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7

Saraví Cisneros, Hebe, Sergio Laurella, Danila L. Ruiz, Agustín Ponzinibbio, Patricia E. Allegretti, and Jorge J. P. Furlong. "Spectrometric Study of the Nitrile-Ketenimine Tautomerism." International Journal of Spectroscopy 2009 (September 9, 2009): 1–18. http://dx.doi.org/10.1155/2009/408345.

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Mass spectrometry is used to evaluate the occurrence of the nitrile-ketenimine tautomerism. Mass spectra of two differently substituted nitriles, ethyl-4,4-dicyano-3-methyl-3-butenoate and diethyl-2-cyano-3-methyl-2-pentenodiate are examined looking for common mass spectral behaviors. Ion fragmentation assignments for specific tautomers allow to predict the presence of the corresponding structures. Additionally, the mass spectrum and nuclear magnetic resonance spectra of ethyl-4,4-dicyano-2,2-diethyl-3-methyl-3-butenoate and that of the corresponding amination product support the occurrence of the ketenimine tautomer in the equilibrium.

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8

Capuano, Lilly, and Keramatollah Djokar. "N-Funktionalisierte Ketenimine, II." Liebigs Annalen der Chemie 1985, no. 12 (December 22, 1985): 2305–12. http://dx.doi.org/10.1002/jlac.198519851202.

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9

Cen, Mengjie, Qiaoyi Xiang, Yiwen Xu, Shengguo Duan, Yaohong Lv, Ze-Feng Xu, and Chuan-Ying Li. "Synthesis of α-cyano sulfone via thermal rearrangement of 1,4-disubstituted triazole mediated by carbene and radical species." Organic Chemistry Frontiers 7, no. 3 (2020): 596–601. http://dx.doi.org/10.1039/c9qo01340g.

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10

Chauhan, Dinesh Pratapsinh, Sreejith J. Varma, Mahesh Gudem, Nihar Panigrahi, Khushboo Singh, Anirban Hazra, and Pinaki Talukdar. "Intramolecular cascade rearrangements of enynamine derived ketenimines: access to acyclic and cyclic amidines." Organic & Biomolecular Chemistry 15, no. 22 (2017): 4822–30. http://dx.doi.org/10.1039/c7ob00499k.

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11

Wolf, Reinhard, Ming Wah Wong, Colin H. L. Kennard, and Curt Wentrup. "A Remarkably Stable Linear Ketenimine." Journal of the American Chemical Society 117, no. 25 (June 1995): 6789–90. http://dx.doi.org/10.1021/ja00130a023.

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12

Alajarin, Mateo, Marta Marin-Luna, and Angel Vidal. "Recent Highlights in Ketenimine Chemistry." European Journal of Organic Chemistry 2012, no. 29 (June 6, 2012): 5637–53. http://dx.doi.org/10.1002/ejoc.201200383.

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13

Xu, Ze-Feng, Xing Yu, Dongdong Yang, and Chuan-Ying Li. "Metal-free synthesis of 2-aminonaphthalenes by intramolecular transannulation of 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles." Organic & Biomolecular Chemistry 15, no. 15 (2017): 3161–64. http://dx.doi.org/10.1039/c7ob00637c.

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A facile metal-free synthesis of 2-aminonaphthalenes by intramolecular transannulation of 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles was realized with the proposed ketenimine as the key intermediate.

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14

Alajarin, Mateo, Baltasar Bonillo, Maria-Mar Ortin, and Angel Vidal. "Ketenimine for Nitrile Rearrangements in N-Arylmethyl Ketenimines: [1,n] Migrations of Bulky Arylmethyl Groups." Letters in Organic Chemistry 7, no. 7 (October 1, 2010): 528–32. http://dx.doi.org/10.2174/157017810793362280.

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15

Li, Guofeng, Man Zhao, Junqiu Xie, Ying Yao, Lingyun Mou, Xiaowei Zhang, Xiaomin Guo, et al. "Efficient synthesis of cyclic amidine-based fluorophores via 6π-electrocyclic ring closure." Chemical Science 11, no. 14 (2020): 3586–91. http://dx.doi.org/10.1039/d0sc00798f.

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Novel 10π-electron cyclic amidines with excellent fluorescence properties were synthesized by a general and efficient 6π-electrocyclic ring closure of ketenimine and imine starting from N-sulfonyl triazoles and arylamines.

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16

Sun, Jiarui, Xiangsheng Cheng, John Kamanda Mansaray, Weihong Fei, Jieping Wan, and Weijun Yao. "A copper-catalyzed three component reaction of aryl acetylene, sulfonyl azide and enaminone to form iminolactone via 6π electrocyclization." Chemical Communications 54, no. 99 (2018): 13953–56. http://dx.doi.org/10.1039/c8cc06868b.

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We developed a copper-catalyzed three component reaction of aryl acetylene, enaminone and sulfonyl azide to construct iminolactone via copper-catalyzed alkyne–azide cycloaddition (CuAAC), Michael addition of metalated ketenimine followed by elimination and 6π electrocyclization.

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17

Wang, Baolin, Kota Koshino, and Rei Kinjo. "Bicyclic (amino)(borata)carbene derived from diazadiborinine and isonitrile." Chemical Communications 55, no. 86 (2019): 13012–14. http://dx.doi.org/10.1039/c9cc06453b.

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The reaction of 1,4,2,5-diazadiborinine (1) with an aryl isonitrile afforded a bicyclic product containing an indole unit (2) or ketenimine moiety (3), suggesting the generation of a B,N-carbene intermediate formed in the initial step.

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18

Honrado, Manuel, Sonia Sobrino, Juan Fernández-Baeza, Luis F. Sánchez-Barba, Andrés Garcés, Agustín Lara-Sánchez, and Ana M. Rodríguez. "Synthesis of an enantiopure scorpionate ligand by a nucleophilic addition to a ketenimine and a zinc initiator for the isoselective ROP of rac-lactide." Chemical Communications 55, no. 61 (2019): 8947–50. http://dx.doi.org/10.1039/c9cc04716f.

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The first example of nucleophilic addition of an organolithium to a ketenimine to prepare an enantiopure NNN-heteroscorpionate ligand is reported. Its utility to induce chirality is verified via preparation of two new zinc complexes, producing highly isotactic poly(lactide)s.

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19

Balueva, A. S., E. R. Mustakimov, G. N. Nikonov, Yu T. Struchkov, A. P. Pisarevsky, and R. R. Musin. "Interaction ofZ-1,2-borylphosphinoalkene with ketenimine." Russian Chemical Bulletin 45, no. 1 (January 1996): 174–79. http://dx.doi.org/10.1007/bf01433757.

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20

Fandos, Rosa, Maurizio Lanfranchi, Antonio Otero, María Angela Pellinghelli, M. José Ruiz, and Jan H. Teuben. "Early-Transition-Metal Ketenimine Complexes: Synthesis, Reactivity, and Structure of Ketenimine-Containing Titanocene and Zirconocene Complexes." Organometallics 16, no. 24 (November 1997): 5283–88. http://dx.doi.org/10.1021/om970568p.

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21

Philippova, Anna N., Daria V. Vorobyeva, Pavel S. Gribanov, Fedor M. Dolgushin, and Sergey N. Osipov. "Diastereoselective Synthesis of Highly Functionalized Proline Derivatives." Molecules 27, no. 20 (October 14, 2022): 6898. http://dx.doi.org/10.3390/molecules27206898.

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An efficient way to access highly functionalized proline derivatives was developed based on a Cu(I)-catalyzed reaction between CF3-substituted allenynes and tosylazide, which involved a cascade of [3 + 2]-cycloaddition/ketenimine and a rearrangement/Alder-ene cyclization to afford the new proline framework with a high diastereoselectivity.

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22

KHLEBNIKOV, A. F., M. S. NOVIKOV, and R. R. KOSTIKOV. "ChemInform Abstract: Ketenimine Ylides in the Reactions of Fluorochloro- and Dibromocarbenes with Ketenimines. Synthesis of Carbamoyl Fluorides." ChemInform 22, no. 9 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199109152.

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23

Alajarin, Mateo, Baltasar Bonillo, Maria-Mar Ortin, and Angel Vidal. "ChemInform Abstract: Ketenimine for Nitrile Rearrangement in N-Arylmethyl Ketenimines: [1,n] Migrations of Bulky Arylmethyl Groups." ChemInform 42, no. 14 (March 14, 2011): no. http://dx.doi.org/10.1002/chin.201114034.

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24

Reva, Igor, Hanna Rostkowska, and Leszek Lapinski. "Phototransformations of 2,3-Diamino-2-Butenedinitrile (DAMN) Monomers Isolated in Low-Temperature Argon Matrix." Photochem 2, no. 2 (June 16, 2022): 448–62. http://dx.doi.org/10.3390/photochem2020031.

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UV-induced transformations were studied for monomers of 2,3-diamino-2-butenedinitrile (DAMN) isolated in argon matrices. Photoinduced hydrogen-atom transfer was found to be the major process occurring upon UV (λ > 320 nm or λ > 295 nm) excitation of matrix-isolated DAMN monomers. As a result of the transfer of a hydrogen atom from an amino group to a nitrile fragment, a tautomer of DAMN involving a ketenimine group was generated. Identification of this photo-produced species was based on comparison of its experimental IR spectrum with the spectrum theoretically predicted for the ketenimine form. Another product photogenerated upon UV (λ > 320 nm, λ > 295 nm, or λ > 270 nm) irradiation of DAMN isolated in Ar matrices was identified as 4-amino-1H-imidazole-5-carbonitrile (AICN). The structure of this photoproduct was unambiguously assigned on the basis of an exact match of wavenumbers of the bands in the IR spectrum of this photogenerated species and the wavenumbers of IR bands of AICN trapped (in a separate experiment) from the gas phase into an Ar matrix.

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25

WOLF, R., M. W. WONG, C. H. L. KENNARD, and C. WENTRUP. "ChemInform Abstract: A Remarkably Stable Linear Ketenimine." ChemInform 26, no. 43 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199543159.

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26

Strecker, Beate, and Helmut Werner. "Ketenimine Complexes from Metal Isocyanides and Diazoalkanes." Angewandte Chemie International Edition in English 29, no. 3 (March 1990): 275–76. http://dx.doi.org/10.1002/anie.199002751.

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27

Alajarin, Mateo, Marta Marin-Luna, and Angel Vidal. "ChemInform Abstract: Recent Highlights in Ketenimine Chemistry." ChemInform 44, no. 13 (March 18, 2013): no. http://dx.doi.org/10.1002/chin.201313208.

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28

Guan, Zhi-Rong, Shuai Liu, Zi-Ming Liu, and Ming-Wu Ding. "One-Pot Three-Component Synthesis of Pyrrolidin-2-ones via a Sequential Wittig/Nucleophilic Addition/Cyclization Reaction." Synthesis 51, no. 11 (March 4, 2019): 2402–8. http://dx.doi.org/10.1055/s-0037-1612279.

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A new efficient synthesis of pyrrolidin-2-ones via sequential Wittig reaction/nucleophilic addition/cyclization was developed. The Wittig reaction of the phosphoranes with isocyanates produced ketenimine intermediates that were then treated with primary amines to give amidines, which were treated with catalytic sodium alkoxide to give 2-imino-5-oxopyrrolidine-3-carboxylates in good yields.

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29

Kumar, Gadi Ranjith, Yalla Kiran Kumar, Ruchir Kant, and Maddi Sridhar Reddy. "Tandem Cu-catalyzed ketenimine formation and intramolecular nucleophile capture: Synthesis of 1,2-dihydro-2-iminoquinolines from 1-(o-acetamidophenyl)propargyl alcohols." Beilstein Journal of Organic Chemistry 10 (May 28, 2014): 1255–60. http://dx.doi.org/10.3762/bjoc.10.125.

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The copper-catalyzed ketenimine formation reaction of 1-(o-acetamidophenyl)propargyl alcohols with various sulfonyl azides is found to undergo a concomitant intramolecular nucleophile attack to generate 1,2-dihydro-2-iminoquinolines after aromatization (via elimination of acetyl and hydroxy groups) and tautomerization. The reaction produces 4-substituted and 3,4-unsubstituted title compounds in moderate to good yields under mild reaction conditions.

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30

Andersen, Heidi Gade, David Kvaskoff, and Curt Wentrup. "Bisiminopropadienes R-N=C=C=C=N-R from Pyridopyrimidines." Australian Journal of Chemistry 65, no. 6 (2012): 686. http://dx.doi.org/10.1071/ch12039.

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Chlorination of the N,N′-di(2-pyridyl)malonamide 13a affords 2-chloro-8-methyl-4-(2-(4-picolinyl)imino-4H-pyrido[1,2-a]pyrimidine 17a. Flash vacuum thermolysis of 17a causes efficient ring opening to the valence-tautomeric ketenimine 18a/19a, elimination of HCl, and formation of the bis(4-methyl-2-pyridyl)iminopropadiene, R-N=C=C=C=N-R 20a.

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31

Wang, Bingze, and Conghao Deng. "Mechanism of the isomerization of azirinylidene to ketenimine." Chemical Physics Letters 142, no. 1-2 (December 1987): 92–95. http://dx.doi.org/10.1016/0009-2614(87)87256-1.

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32

Liu, Yun-Lin, Guo-Shu Chen, and Xiao-Tong Lin. "3-(2-Isocyanoethyl)indole: A Versatile Reagent for Polycyclic Spiroindoline Synthesis." Synlett 31, no. 11 (March 12, 2020): 1033–39. http://dx.doi.org/10.1055/s-0039-1690853.

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Polycyclic spiroindolines are the basic skeletons of large families of indole alkaloids that exhibit a broad spectrum of biological and pharmacological activities. The past seven years have seen impressive developments in the construction of polycyclic spiroindolines enabled by 3-(2-isocyanoethyl)indole-based cascade reactions. We herein give a brief summary on this evolution and highlight our contributions in this field.1 Introduction2 Cascade Reactions Involving Nitrilium Ion Intermediates3 Cascade Reactions Involving Ketenimine Intermediates4 Conclusion and Outlook

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33

Wentrup, Curt, Ales Reisinger, and David Kvaskoff. "4-Pyridylnitrene and 2-pyrazinylcarbene." Beilstein Journal of Organic Chemistry 9 (April 17, 2013): 754–60. http://dx.doi.org/10.3762/bjoc.9.85.

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Both flash vacuum thermolysis (FVT) and matrix photolysis generate 2-diazomethylpyrazine (22) from 1,2,3-triazolo[1,5-a]pyrazine (24). FVT of 4-azidopyridine (18) as well as of 24 or 2-(5-tetrazolyl)pyrazine (23) affords the products expected from the nitrene, i.e., 4,4’-azopyridine and 2- and 3-cyanopyrroles. Matrix photolyses of both 18 and 24 result in ring expansion of 4-pyridylnitrene/2-pyrazinylcarbene to 1,5-diazacyclohepta-1,2,4,6-tetraene (20). Further photolysis causes ring opening to the ketenimine 27.

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34

Huang, Jie, Feng Li, Lei Cui, Shikuan Su, Xueshun Jia, and Jian Li. "Palladium-catalyzed cascade reactions of enynones and isocyanides: access towards functionalized ketenimine and its application." Chemical Communications 56, no. 33 (2020): 4555–58. http://dx.doi.org/10.1039/c9cc09363j.

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35

Degli Esposti, C., L. Dore, and L. Bizzocchi. "Accurate rest-frequencies of ketenimine (CH2CNH) at submillimetre wavelength." Astronomy & Astrophysics 565 (May 2014): A66. http://dx.doi.org/10.1051/0004-6361/201423589.

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36

Lee, Vladimir Ya, Henri Ranaivonjatovo, Jean Escudié, Jacques Satgé, Antoine Dubourg, Jean-Paul Declercq, Mikhail P. Egorov, and Oleg M. Nefedov. "An Eight-Membered CyclicC,N-Bis(germadiyl) Bis(ketenimine)." Organometallics 17, no. 8 (April 1998): 1517–22. http://dx.doi.org/10.1021/om971014p.

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37

Rodler, M., R. D. Brown, P. D. Godfrey, and B. Kleibömer. "The rotation-inversion spectrum of ketenimine, H2CCNH." Journal of Molecular Spectroscopy 118, no. 1 (July 1986): 267–76. http://dx.doi.org/10.1016/0022-2852(86)90240-7.

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38

BALUEVA, A. S., E. R. MUSTAKIMOV, G. N. NIKONOV, YU T. STRUCHKOV, A. P. PISAREVSKII, and R. R. MUSIN. "ChemInform Abstract: Reaction of (E)-1,2-Borylphoshinoalkene with Ketenimine." ChemInform 27, no. 26 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199626217.

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39

Kvaskoff, David, Ullrich Mitschke, Chris Addicott, Justin Finnerty, Pawel Bednarek, and Curt Wentrup. "Interconversion of Nitrenes, Carbenes, and Nitrile Ylides by Ring Expansion, Ring Opening, Ring Contraction, and Ring Closure: 3-Quinolylnitrene, 2-Quinoxalylcarbene, and 3-Quinolylcarbene." Australian Journal of Chemistry 62, no. 3 (2009): 275. http://dx.doi.org/10.1071/ch08523.

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Photolysis of 3-azidoquinoline 6 in an Ar matrix generates 3-quinolylnitrene 7, which is characterized by its electron spin resonance (ESR), UV, and IR spectra in Ar matrices. Nitrene 7 undergoes ring opening to a nitrile ylide 19, also characterized by its UV and IR spectra. A subsequent 1,7-hydrogen shift in the ylide 19 affords 3-(2-isocyanophenyl)ketenimine 20. Matrix photolysis of 1,2,3-triazolo[1,5-c]quinoxaline 26 generates 4-diazomethylquinazoline 27, followed by 4-quinazolylcarbene 28, which is characterized by ESR and IR spectroscopy. Further photolysis of carbene 28 slowly generates ketenimine 20, thus suggesting that ylide 19 is formed initially. Flash vacuum thermolysis (FVT) of both 6 and 26 affords 3-cyanoindole 22 in high yield, thereby indicating that carbene 28 and nitrene 7 enter the same energy surface. Matrix photolysis of 3-quinolyldiazomethane 30 generates 3-quinolylcarbene 31, which on photolysis at >500 nm reacts with N2 to regenerate diazo compound 30. Photolysis of 30 in the presence of CO generates a ketene (34). 3-Quinolylcarbene 31 cyclizes on photolysis at >500 nm to 5-aza-2,3-benzobicyclo[4.1.0]hepta-2,4,7-triene 32. Both 31 and 32 are characterized by their IR and UV spectra. FVT of 30 yields a mixture of 2- and 3-cyanoindenes via a carbene–carbene–nitrene rearrangement 31 → 2-quinolylcarbene 39 → 1-naphthylnitrene 43. The reaction mechanisms are supported by density functional theory calculations of the energies and spectra of all relevant ground and transition state structures at the B3LYP/6–31G* level.

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40

Escandón-Mancilla, Flor María, Alberto Cedillo-Cruz, Raúl Eduardo Gordillo-Cruz, Diego Martínez-Otero, M. V. Basavanag Unnamatla, and Erick Cuevas-Yañez. "N-(p-Toluenesulfonyl)-1-(4′-acetylphenoxy)acrylimidate: Synthesis, Crystal Structure and Theoretical Studies." Molbank 2022, no. 4 (November 28, 2022): M1509. http://dx.doi.org/10.3390/m1509.

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The formation of N-sulfonyl-1-aryloxy acrylimidate is described, for the first time, from a consecutive process, which involves a CuAAC reaction, a ketenimine formation and subsequent rearrangement between an aryl propargyl ether and a sulfonyl azide. The structure of this newly synthesized compound was analyzed by NMR spectra and unambiguously established by X-ray analysis. In addition, theoretical calculations, which included a Hirshfeld surface, FMO, QTAIM and NCI indices analysis, corroborated the formation of π-π stacking interactions among aromatic rings, as well as C-H···O interactions between vinyl hydrogens with ketone carbonyl oxygen.

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41

刘, 燕萍. "Recent Progress of [3,3]-Rearrangement Reaction of Allyl Ketenimine Structure." Journal of Organic Chemistry Research 09, no. 04 (2021): 50–58. http://dx.doi.org/10.12677/jocr.2021.94007.

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42

Osman, O. I. "Theoretical and Computational Study of Tautomerization of Ketenimine to Acetonitrile." Asian Journal of Chemistry 27, no. 8 (2015): 3091–96. http://dx.doi.org/10.14233/ajchem.2015.18907.

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43

Ruiz, Javier, Marta P. Gonzalo, Marilín Vivanco, M. Rosario Díaz, and Santiago García-Granda. "A three-component reaction involving isocyanide, phosphine and ketenimine functionalities." Chemical Communications 47, no. 14 (2011): 4270. http://dx.doi.org/10.1039/c0cc05025c.

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44

Rahim, Marufur, Nicholas J. Taylor, Shixuan Xin, and Scott Collins. "Synthesis and Structure of Acyclic Bis(ketenimine) Complexes of Zirconium." Organometallics 17, no. 7 (March 1998): 1315–23. http://dx.doi.org/10.1021/om970862h.

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45

Yavari, Issa, and Daryoush Tahmassebi. "Configurational Properties of Eight-membered Rings Containing Two Ketenimine Units." Journal of Chemical Research, no. 12 (1998): 782–83. http://dx.doi.org/10.1039/a804014a.

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46

Shustov, G. V., A. V. Kachanov, and R. G. Kostyanovskii. "Ketenimine-nitrile rearrangements of N-alkoxyketenimines under their generation conditions." Bulletin of the Russian Academy of Sciences Division of Chemical Science 41, no. 11 (November 1992): 2039–45. http://dx.doi.org/10.1007/bf00863370.

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47

Zhao, Hongyang, Yanpeng Xing, Ping Lu, and Yanguang Wang. "Synthesis of 2,3-Disubstituted Quinolines via Ketenimine or Carbodiimide Intermediates." Chemistry - A European Journal 22, no. 42 (September 5, 2016): 15144–50. http://dx.doi.org/10.1002/chem.201603074.

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48

BESTMANN, H. J., and H. LEHNEN. "ChemInform Abstract: Synthesis and Reactions of N-Phenylbis(diethylphosphonato)ketenimine." ChemInform 23, no. 20 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199220248.

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49

Weragoda, Geethika K., Anushree Das, Sujan K. Sarkar, H. Dushanee M. Sriyarathne, Xiaoming Zhang, Bruce S. Ault, and Anna D. Gudmundsdottir. "Singlet Photoreactivity of 3-Methyl-2-phenyl-2H-azirine." Australian Journal of Chemistry 70, no. 4 (2017): 413. http://dx.doi.org/10.1071/ch16604.

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Abstract:

Irradiation of 3-methyl-2-phenyl-2H-azirine (1) at 254 nm in argon matrices results in ylide 6. Similarly, laser flash photolysis (λ = 266 nm) of azirine 1 in acetonitrile yields ylide 6, which has a transient absorption with λmax at ~340 nm and a lifetime of 14 μs. Density functional theory calculations were preformed to support the characterisation of ylide 6 in solution and argon matrices. Irradiation of azirine 1 above 300 nm has previously been reported (J. Org. Chem. 2014, 79, 653) to yield triplet vinylnitrene in solution and ketenimine in cryogenic argon matrices. Thus, the photochemistry of azirine 1 is dependent on the irradiation wavelength.

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50

He, Wenxing, Weihua Wang, Xiaojun Tan, and Ping Li. "Theoretical study on the cycloaddition reaction mechanism between ketenimine and acetonitrile." Main Group Chemistry 15, no. 3 (September 15, 2016): 221–30. http://dx.doi.org/10.3233/mgc-160201.

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