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Journal articles on the topic 'Cyclohexenones'

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Published: 4 June 2021

Last updated: 4 March 2023

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1

Okoth, Dorothy A., and Neil A. Koorbanally. "Cardanols, Long Chain Cyclohexenones and Cyclohexenols from Lannea schimperi (Anacardiaceae)." Natural Product Communications 10, no. 1 (January 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000126.

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Alkenyl cyclohexenones (1a-d), alkenyl cyclohexenols (2a-c and 3b-d) and cardanols (4a-d) were isolated from the stem bark and root of Lannea schimperi. The alkenyl cyclohexenones (1a and 1d) and cardanols (4a and 4d) have side chains which have not been reported previously, in combination with the core skeletal structures. In addition, compounds 2a-c and 3b-d are all new cyclohexenols. Also isolated were the triterpenes, taraxerone and taraxerol, and sitosterol. The suite of compounds isolated (cyclohexenones and cyclohexenols) make up a nice biosynthetic pathway to the cardanols. The 5-[alkenyl]-4,5-dihydroxycyclohex-2-enone mixture (1a-d) exhibited good in vitro cytotoxicity against the Chinese Hamster Ovarian mammalian cell-line. The compounds were identified mainly from GCMS and NMR spectroscopic techniques.

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2

Hylden, Anne T., Eric J. Uzelac, Zeljko Ostojic, Ting-Ting Wu, Keely L. Sacry, Krista L. Sacry, Lin Xi, and T. Nicholas Jones. "Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones." Beilstein Journal of Organic Chemistry 7 (September 23, 2011): 1323–26. http://dx.doi.org/10.3762/bjoc.7.155.

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The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2-cyclohexenones proceeds in good yields (58–90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy-2-cyclohexenones.

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3

Davis, BR, MG Hinds, and SJ Johnson. "Diterpene Synthesis. III. Acid-Catalyzed Cyclization of Methoxyphenylethyltrimethyl-Cyclohexanols, Cyclohexenols and Cyclohexenones." Australian Journal of Chemistry 38, no. 12 (1985): 1815. http://dx.doi.org/10.1071/ch9851815.

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Cyclization of the methoxyphenylethyltrimethylcyclohexanols (3), (4) and (5), the cyclohexenols (6) and (7) and the cyclohexenones (20) and (21), in the presence of a variety of acids, has been studied and the products analysed by chromatographic and spectroscopic techniques. Both cis - and trans-podocarpa-8,11,13-trienes are formed, along with the rearranged compounds (16), (17) and (30). These results parallel our earlier findings and contrast with some reports in the literature.

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4

Schuster, David I., Jie-Min Yang, Jan Woning, Timothy A. Rhodes, and Anton W. Jensen. "Mechanism of acid-catalyzed photoaddition of methanol to 3-alkyl2-cyclohexenones." Canadian Journal of Chemistry 73, no. 11 (November 1, 1995): 2004–10. http://dx.doi.org/10.1139/v95-247.

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Contrary to a previous report, it is concluded that formation of methanol adducts to 3-methyl-2-cyclohexenones and of deconjugated enones on irradiation of the enones in acidified solutions proceeds via protonation of the intermediate enone π,π* triplet excited state and not by protonation of a relatively long-lived ground state trans-cyclohexenone. A rate constant for protonation of the triplet state of 3-methyl-2-cyclohexenone by sulfuric acid of 1.7 × 109 M−1 s−1 was determined by laser flash photolysis in ethyl acetate. Based on quantum efficiencies of product formation, a rate constant of ca. 108 M−1 s−1 was estimated for protonation of the enone triplet by acetic acid, which is too small to cause measurable reduction in the triplet state lifetime in the mM concentration range used in the preparative studies. The intermediate carbocation can be trapped by methanol, or revert to starting enone or the exocyclic deconjugated enone by loss of a proton. Since products revert to starting materials in an acid-catalyzed process, there is an acid concentration at which the yields of products are optimal. This concentration is ca. 6 mM for acetic acid, but is only 0.1 mM for p-toluenesulfonic or sulfuric acids. Product formation could be quenched using 1-methylnaphthalene and cyclopentene as triplet quenchers; in the latter case, formation of [2 + 2] photoadducts was observed to compete with formation of methanol adducts. Quenching rate constants were determined by laser flash studies. Keywords: laser flash photolysis, kinetic absorption spectroscopy (KAS), photoacoustic calorimetry (PAC), protonation of triplet states, trans-cyclohexenones.

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5

Weir, D., J. C. Scaiano, and D. I. Schuster. "A reinvestigation of the interaction between triplet states of cyclohexenones and amines." Canadian Journal of Chemistry 66, no. 10 (October 1, 1988): 2595–600. http://dx.doi.org/10.1139/v88-407.

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Laser flash photolysis studies lead to the conclusion that the short-lived triplet states of cyclohexenones are readily quenched by amines. For example, in the case of 2-cyclohexen-1-one (1) its triplet state (τT = 40 ns in acetonitrile) is quenched by triethylamine with a rate constant of (9.0 ± 0.8) × 107 M−1 s−1. Cyclohexenone triplets are also quenched efficiently by DABCO and by triphenylamine leading to the formation of the corresponding amine radical cations. The new evidence reported rules out the involvement of long-lived detectable exciplexes.

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6

Helmchen, G., G. Franck, and K. Brödner. "Enantioselective Synthesis of Cyclohexenones." Synfacts 2010, no. 10 (September 22, 2010): 1166. http://dx.doi.org/10.1055/s-0030-1258649.

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7

VERHE, R. "ChemInform Abstract: 3-Isobutoxy-2-cyclohexenone: A Versatile Synthon for the Regiospecific Alkylation of Cyclohexenones." ChemInform 24, no. 52 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199352309.

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8

Das, Manik, and Kuntal Manna. "Bioactive Cyclohexenones: A Mini Review." Current Bioactive Compounds 11, no. 4 (December 30, 2015): 239–48. http://dx.doi.org/10.2174/157340721104151230104138.

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9

Holmes, Andrew B., and Nigel C. Madge. "Synthesis of 4,4-disubstituted cyclohexenones." Tetrahedron 45, no. 3 (January 1989): 789–802. http://dx.doi.org/10.1016/0040-4020(89)80110-3.

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10

Clot-Almenara, Lidia, Carles Rodríguez-Escrich, and Miquel A. Pericàs. "Desymmetrisation of meso-diones promoted by a highly recyclable polymer-supported chiral phosphoric acid catalyst." RSC Advances 8, no. 13 (2018): 6910–14. http://dx.doi.org/10.1039/c7ra13471a.

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11

Samser, Shaikh, Priyabrata Biswal, Sushanta Kumar Meher, and Krishnan Venkatasubbaiah. "Palladium mediated one-pot synthesis of 3-aryl-cyclohexenones and 1,5-diketones from allyl alcohols and aryl ketones." Organic & Biomolecular Chemistry 19, no. 6 (2021): 1386–94. http://dx.doi.org/10.1039/d0ob02515a.

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12

Zaidlewicz, M., W. Sokól, A. Wolan, J. Cytarska, A. Tafelska-Kaczmarek, A. Dzielendziak, and A. Prewysz-Kwinto. "Enolboration of conjugated ketones and synthesis of beta-amino alcohols and boronated alpha-amino acids." Pure and Applied Chemistry 75, no. 9 (January 1, 2003): 1349–55. http://dx.doi.org/10.1351/pac200375091349.

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Enolization–aldolization of conjugated ketones, enantioselective synthesis of benzofuryl beta-amino alcohols, and synthesis of p-dihydroxyborylphenylalanine (BPA) and its analogs are described. Aldolization of benzaldehyde with lithium dienolates derived from unhindered conjugated cyclohexenones favored anti- selectivity, whereas syn selectivity was favored for hindered cyclohexenones. Anti-aldols were preferentially formed from dienolborinates derived from conjugated cyklohexenones, however,competing aldolization at the 2-position was observed for hindered ketones. Benzofuryl beta-amino alcohols were prepared using as a key step the enantioselective reduction of the corresponding alpha-bromoacetylbenzofurans with (–)-B- -chlorodiisopinocampheylborane. Ionic liquids were used as solvents for the synthesis of BPA by the Suzuki cross-coupling reaction. The reaction time is short, and a solution of the catalyst in the ionic liquid can be recycled.

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13

Podraza, Kenneth F. "REGIOSPECIFIC ALKYLATION OF CYCLOHEXENONES. A REVIEW." Organic Preparations and Procedures International 23, no. 2 (April 1991): 217–35. http://dx.doi.org/10.1080/00304949109458319.

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14

Kündig, E., Manisankar Sau, and Alejandro Perez-Luna. "Synthesis of 4,5-trans-Substituted Cyclohexenones." Synlett 2006, no. 13 (August 2006): 2114–18. http://dx.doi.org/10.1055/s-2006-948187.

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15

MIYAOKA, Hiroaki, Shoichi SAGAWA, Tadamichi INOUE, Hiroto NAGAOKA, and Yasuji YAMADA. "Efficient synthesis of optically active cyclohexenones." CHEMICAL & PHARMACEUTICAL BULLETIN 42, no. 2 (1994): 405–7. http://dx.doi.org/10.1248/cpb.42.405.

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16

PODRAZA, K. F. "ChemInform Abstract: Regiospecific Alkylation of Cyclohexenones." ChemInform 22, no. 45 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199145353.

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17

Meister, Anne C., Paul F. Sauter, and Stefan Bräse. "A Stereoselective Approach to Functionalized Cyclohexenones." European Journal of Organic Chemistry 2013, no. 31 (September 13, 2013): 7110–16. http://dx.doi.org/10.1002/ejoc.201300752.

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18

Yang, Hongzhou, Qingqing Wang, Yuan Luo, Ling Ye, Xinying Li, Feng Chen, Zhigang Zhao, and Xuefeng Li. "Enantioselective synthesis of trifluoromethyl substituted cyclohexanones via an organocatalytic cascade Michael/aldol reaction." Organic & Biomolecular Chemistry 18, no. 8 (2020): 1607–11. http://dx.doi.org/10.1039/d0ob00004c.

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19

Feigenbaum, Alexandre, Yves Fort, Jean Pierre Pete, and Denise Scholler. "Photochemical cyclization of 2-alkyl-3-aryl-2-cyclohexenones and 2-alkoxy-3-aryl-2-cyclohexenones." Journal of Organic Chemistry 51, no. 23 (November 1986): 4424–32. http://dx.doi.org/10.1021/jo00373a015.

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20

Wen, Zhen-Kang, Xiao-Xue Wu, Wen-Kai Bao, Jing-Jing Xiao, and Jian-Bin Chao. "Palladium-Catalyzed Regioselective Coupling Cyclohexenone into Indoles: Atom-Economic Synthesis of β-Indolyl Cyclohexenones and Derivatization Applications." Organic Letters 22, no. 12 (June 9, 2020): 4898–902. http://dx.doi.org/10.1021/acs.orglett.0c01763.

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21

Liang, Yu-Feng, Song Song, Lingsheng Ai, Xinwei Li, and Ning Jiao. "A highly efficient metal-free approach to meta- and multiple-substituted phenols via a simple oxidation of cyclohexenones." Green Chemistry 18, no. 24 (2016): 6462–67. http://dx.doi.org/10.1039/c6gc02674e.

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The simple and readily available I₂ catalyst, and a cheap and common DMSO oxidant could be employed for the transformation of cyclohexenones to meta- and multiple-substituted phenols with significant tolerance to various functional substituents.

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22

Liu, Cheng-Hang, and Zhi-Xiang Yu. "Rh-catalysed [5 + 1] cycloaddition of allenylcyclopropanes and CO: reaction development and application to the formal synthesis of (−)-galanthamine." Organic & Biomolecular Chemistry 14, no. 25 (2016): 5945–50. http://dx.doi.org/10.1039/c6ob00660d.

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A Rh-catalyzed [5 + 1] cycloaddition of allenylcyclopropanes and CO has been developed to synthesize functionalized 2-methylidene-3,4-cyclohexenones. This cycloaddition reaction has been utilized as a key step in the formal synthesis of natural product (−)-galanthamine.

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23

Zhang, Jingwu, Qiangqiang Jiang, Dejun Yang, Xiaomei Zhao, Yanli Dong, and Renhua Liu. "Reaction-activated palladium catalyst for dehydrogenation of substituted cyclohexanones to phenols and H2 without oxidants and hydrogen acceptors." Chemical Science 6, no. 8 (2015): 4674–80. http://dx.doi.org/10.1039/c5sc01044f.

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A combination of Pd/C and H₂ is found to dehydrogenate a wide range of substituted cyclohexanones and 2-cyclohexenones to their corresponding phenols with high isolated yields, with H₂ as the only byproduct.

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24

Liu, Xueli, Jun Chen, and Tianlin Ma. "Catalytic dehydrogenative aromatization of cyclohexanones and cyclohexenones." Organic & Biomolecular Chemistry 16, no. 45 (2018): 8662–76. http://dx.doi.org/10.1039/c8ob02351d.

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Prompted by the scant attention paid by published literature reviews to the comprehensive catalytic dehydrogenative aromatization of cyclohexa(e)nones, this review describes recent methods developed to-date involving transition-metal-catalyzed oxidative aromatization and metal-free strategies for the transformation of cyclohexa(e)nones to substituted phenols.

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25

Adembri, Giorgio, Mirella Scotton, and Alessandro Sega. "The crystal structure and stereochemistry of 2-acetyl-3,5,6-trihydroxy-5,6-dimethyl-2-cyclohexenones." Canadian Journal of Chemistry 66, no. 2 (February 1, 1988): 246–48. http://dx.doi.org/10.1139/v88-041.

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The stereochemistry of 3a, one of the 2-acetyl-3,5,6-trihydroxy-5,6-dimethylcyclohexenones, obtained by rearrangement of 2,3-diacetyl-4-hydroxy-4-methylcyclopentenone, 2a, under basic conditions, was determined by an X-ray crystal structure analysis. An ORTEP plot shows the configuration of (5RS,6RS)-2-acetyl-3,5,6-trihydroxy-5,6-dimethylcyclohexenone and the presence of a conjugated chelated system involving the H-bonding between O(3)… H(31) and H(31)… O(2).Crystals of 3a are triclinic, a = 10.979(4), b = 7.766(3), c = 6.382(3) Å, α = 86.23(2), β = 72.86(1), γ = 88.23(2)°, Z = 2, space group [Formula: see text]. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.036 and Rw = 0.039 for 1324 reflections with I > 3σ(I).The structure of 3a consists of centrosymmetric dimers which contain a nearly planar bicyclic system of a cyclohexenone moiety and a chelated system (Scheme 2).The pathway of the reaction allows one to put forward some hypothesis on the stereochemistry of some analogues of the cyclohexenones 3a and 3b.Faisant appel à la diffraction des rayons-X, on a déterminé la stéréochimie du composé 3a, une des acétyl-2 trihydroxy-3,5,6 diméthyl-5,6 cyclohexénones obtenues par une transposition de la diacétyl-2,3 hydroxy-4 méthyl-4 cyclopenténone, 2a, en milieu alcalin. Une courbe ORTEP démontre que la configuration est (5RS,6RS) pour l'acétyl-2 trihydroxy-3,5,6 diméthyl-5,6 cyclohexénone et qu'il existe un système de chélation conjugué impliquant des liaisons hydrogènes entre O(3)… H(31) et H(31)… O(2).

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26

Piovano, Marisa, Juan Garbarino, Lamberto Tomassini, and Marcello Nicoletti. "Cyclohexanones from Mimulus glabratus and M. luteus." Natural Product Communications 4, no. 12 (December 2009): 1934578X0900401. http://dx.doi.org/10.1177/1934578x0900401204.

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The phytochemical study of Mimulus glabratus A. Gray allowed the isolation of two cyclohexenones: the new compound 6-chlorohalleridone 1 and halleridone 2. Halleridone was also identified in Mimulus luteus L., together with dihydroalleridone 3, the naphtoquinone α-dunnione 4, ursolic acid and β-sitosterol.

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27

Roy, Joyeeta, Tanushree Mal, Supriti Jana, and Dipakranjan Mal. "Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins." Beilstein Journal of Organic Chemistry 12 (March 16, 2016): 531–36. http://dx.doi.org/10.3762/bjoc.12.52.

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Dibromobenzoisofuranone 12, synthesized in six steps, was regiospecifically annulated with 5-substituted cyclohexenones 13/36 in the presence of LiOt-Bu to give brominated anthraquinones 14/38 in good yields. Darzens condensation of 30 was shown to give chain-elongated anthraquinone 32. Alkaline hydrolysis of 38 furnished 39 representing desulfoproisocrinin F.

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28

Usami, Hisanao, Katsuhiko Takagi, and Yasuhiko Sawaki. "Regioselective Photocyclodimerization of Cyclohexenones Intercalated on Clay Layers." Chemistry Letters 21, no. 8 (August 1992): 1405–8. http://dx.doi.org/10.1246/cl.1992.1405.

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29

Hexum, Joseph K., Rodolfo Tello-Aburto, Nicholas B. Struntz, Andrew M. Harned, and Daniel A. Harki. "Bicyclic Cyclohexenones as Inhibitors of NF-κB Signaling." ACS Medicinal Chemistry Letters 3, no. 6 (May 11, 2012): 459–64. http://dx.doi.org/10.1021/ml300034a.

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30

Chong, Byong-Don, Yong-Il Ji, Seong-Soo Oh, Jae-Deuk Yang, Woonphil Baik, and Sangho Koo. "Highly Efficient Synthesis of Methyl-Substituted Conjugate Cyclohexenones." Journal of Organic Chemistry 62, no. 26 (December 1997): 9323–25. http://dx.doi.org/10.1021/jo970145x.

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31

Tian, Jie-Feng, Ru-Jian Yu, Xiao-Xia Li, Hao Gao, Dan Hu, Liang-Dong Guo, Jin-Shan Tang, and Xin-Sheng Yao. "Cyclohexenones and isocoumarins from an endophytic fungus ofSarcosomataceaesp." Journal of Asian Natural Products Research 17, no. 5 (May 4, 2015): 550–58. http://dx.doi.org/10.1080/10286020.2015.1043904.

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32

Kraus, George, and Junwon Kim. "A Direct Preparation of 6-Methylene-2-cyclohexenones." Synthesis 2004, no. 11 (July 22, 2004): 1737–38. http://dx.doi.org/10.1055/s-2004-829162.

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33

Barluenga, J., M. Suero, R. De la Campa, and J. Flórez. "Synthesis of Chiral Cyclohexenones Using a Multicomponent Reaction." Synfacts 2011, no. 02 (January 19, 2011): 0179. http://dx.doi.org/10.1055/s-0030-1259345.

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34

Houjeiry, Tania I., Sarah L. Poe, and D. Tyler McQuade. "Synthesis of Optically Active 4-Substituted 2-Cyclohexenones." Organic Letters 14, no. 17 (August 17, 2012): 4394–97. http://dx.doi.org/10.1021/ol301874x.

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35

MIYAOKA, H., S. SAGAWA, T. INOUE, H. NAGAOKA, and Y. YAMADA. "ChemInform Abstract: Efficient Synthesis of Optically Active Cyclohexenones." ChemInform 25, no. 37 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199437030.

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36

Meister, Anne C., Paul E. Sauter, and Stefan Braese. "ChemInform Abstract: A Stereoselective Approach to Functionalized Cyclohexenones." ChemInform 45, no. 12 (March 6, 2014): no. http://dx.doi.org/10.1002/chin.201412055.

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37

Ren, Hong-Xia, Xiang-Jia Song, Lin Wu, Zhi-Cheng Huang, Ying Zou, Xia Li, Xiao-Wen Chen, Fang Tian, and Li-Xin Wang. "Substituted (E )-2-Methylene-3,4-cyclohexenones through Direct and Convenient Synthesis from Cyclohexenone-MBH Alcohol in the Presence of DMAP." European Journal of Organic Chemistry 2019, no. 4 (December 27, 2018): 715–19. http://dx.doi.org/10.1002/ejoc.201801301.

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38

Ayer, William A., Türkan Gökdemir, Shichang Miao, and Latchezar S. Trifonov. "Leptosphaerones A and B, New Cyclohexenones from Leptosphaeria herpotrichoides." Journal of Natural Products 56, no. 9 (September 1993): 1647–50. http://dx.doi.org/10.1021/np50099a034.

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39

Peña, Javier, Ana B. Antón, Rosalina F. Moro, Isidro S. Marcos, Narciso M. Garrido, and D. Díez. "Tandem catalysis for the synthesis of 2-alkylidene cyclohexenones." Tetrahedron 67, no. 43 (October 2011): 8331–37. http://dx.doi.org/10.1016/j.tet.2011.08.068.

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40

Differding, Edmond, Oscar Vandevelde, Bertrand Roekens, Tran Trieu Van, and Léon Ghosez. "A versatile method of synthesis of anilines and cyclohexenones." Tetrahedron Letters 28, no. 4 (January 1987): 397–400. http://dx.doi.org/10.1016/s0040-4039(00)95738-1.

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41

Lechuga-Eduardo, Harim, Eduardo Zarza-Acuña, and Moisés Romero-Ortega. "Synthesis of 3-substituted 2-cyclohexenones through umpoled functionalization." Tetrahedron Letters 58, no. 33 (August 2017): 3234–37. http://dx.doi.org/10.1016/j.tetlet.2017.07.007.

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42

Carlone, Armando, Mauro Marigo, Chris North, Aitor Landa, and Karl Anker Jørgensen. "A simple asymmetric organocatalytic approach to optically active cyclohexenones." Chem. Commun., no. 47 (2006): 4928–30. http://dx.doi.org/10.1039/b611366d.

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43

PATTERSON, J. W. "ChemInform Abstract: The Alkylation of 3-Chloro-2-cyclohexenones." ChemInform 23, no. 41 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199241112.

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44

ASAOKA, Morio, and Hisashi TAKEI. "The chemistry of (R)- and (S)-5-trimethylsilyl-2-cyclohexenones." Journal of Synthetic Organic Chemistry, Japan 48, no. 3 (1990): 216–28. http://dx.doi.org/10.5059/yukigoseikyokaishi.48.216.

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45

Chênevert, Robert, and Daniel Chamberland. "INFLUENCE OF CYCLODEXTRINS ON THE SODIUM BOROHYDRIDE REDUCTION OF CYCLOHEXENONES." Chemistry Letters 14, no. 8 (August 5, 1985): 1117–18. http://dx.doi.org/10.1246/cl.1985.1117.

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46

Chêneverst, Robert, and Guy Ampleman. "SODIUM BOROHYDRIDE REDUCTION OF CYCLOHEXENONES IN THE PRESENCE OF AMYLOSE." Chemistry Letters 14, no. 10 (October 5, 1985): 1489–90. http://dx.doi.org/10.1246/cl.1985.1489.

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47

Bracher, Franz, and André Gehring. "A Convenient Conversion of Substituted Cyclohexenones into Aryl Methyl Ketones." Synthesis 44, no. 15 (June 29, 2012): 2441–47. http://dx.doi.org/10.1055/s-0032-1316560.

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48

Al-Bogami, Abdullah S., Hamad Z. Alkhathlan, and Tamer S. Saleh. "Microwave Enhanced Green Synthesis of 2-Pyrazolines, Isoxazolines and Cyclohexenones." Asian Journal of Chemistry 25, no. 11 (2013): 6427–33. http://dx.doi.org/10.14233/ajchem.2013.15070.

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49

Taber, Douglass F., Kazuo Kanai, Qin Jiang, and Gina Bui. "Enantiomerically Pure Cyclohexenones by Fe-Mediated Carbonylation of Alkenyl Cyclopropanes." Journal of the American Chemical Society 122, no. 28 (July 2000): 6807–8. http://dx.doi.org/10.1021/ja994155m.

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50

Asaoka, Morio, Toshiaki Aida, Syuzo Sonoda, and Hisashi Takei. "Enantioselective routes to 2,5-disubstituted- and 4-substituted-2-cyclohexenones." Tetrahedron Letters 30, no. 50 (1989): 7075–78. http://dx.doi.org/10.1016/s0040-4039(01)93427-6.

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