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Data publikacji: 4 czerwca 2021
Data aktualizacji: 4 marca 2023

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1

Okoth, Dorothy A., i Neil A. Koorbanally. "Cardanols, Long Chain Cyclohexenones and Cyclohexenols from Lannea schimperi (Anacardiaceae)". Natural Product Communications 10, nr 1 (styczeń 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 i T. Nicholas Jones. "Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones". Beilstein Journal of Organic Chemistry 7 (23.09.2011): 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 i SJ Johnson. "Diterpene Synthesis. III. Acid-Catalyzed Cyclization of Methoxyphenylethyltrimethyl-Cyclohexanols, Cyclohexenols and Cyclohexenones". Australian Journal of Chemistry 38, nr 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 i Anton W. Jensen. "Mechanism of acid-catalyzed photoaddition of methanol to 3-alkyl2-cyclohexenones". Canadian Journal of Chemistry 73, nr 11 (1.11.1995): 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 i D. I. Schuster. "A reinvestigation of the interaction between triplet states of cyclohexenones and amines". Canadian Journal of Chemistry 66, nr 10 (1.10.1988): 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 i K. Brödner. "Enantioselective Synthesis of Cyclohexenones". Synfacts 2010, nr 10 (22.09.2010): 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, nr 52 (19.08.2010): no. http://dx.doi.org/10.1002/chin.199352309.

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8

Das, Manik, i Kuntal Manna. "Bioactive Cyclohexenones: A Mini Review". Current Bioactive Compounds 11, nr 4 (30.12.2015): 239–48. http://dx.doi.org/10.2174/157340721104151230104138.

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9

Holmes, Andrew B., i Nigel C. Madge. "Synthesis of 4,4-disubstituted cyclohexenones". Tetrahedron 45, nr 3 (styczeń 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 i Miquel A. Pericàs. "Desymmetrisation of meso-diones promoted by a highly recyclable polymer-supported chiral phosphoric acid catalyst". RSC Advances 8, nr 13 (2018): 6910–14. http://dx.doi.org/10.1039/c7ra13471a.

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11

Samser, Shaikh, Priyabrata Biswal, Sushanta Kumar Meher i 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, nr 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 i A. Prewysz-Kwinto. "Enolboration of conjugated ketones and synthesis of beta-amino alcohols and boronated alpha-amino acids". Pure and Applied Chemistry 75, nr 9 (1.01.2003): 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, nr 2 (kwiecień 1991): 217–35. http://dx.doi.org/10.1080/00304949109458319.

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14

Kündig, E., Manisankar Sau i Alejandro Perez-Luna. "Synthesis of 4,5-trans-Substituted Cyclohexenones". Synlett 2006, nr 13 (sierpień 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 i Yasuji YAMADA. "Efficient synthesis of optically active cyclohexenones." CHEMICAL & PHARMACEUTICAL BULLETIN 42, nr 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, nr 45 (22.08.2010): no. http://dx.doi.org/10.1002/chin.199145353.

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17

Meister, Anne C., Paul F. Sauter i Stefan Bräse. "A Stereoselective Approach to Functionalized Cyclohexenones". European Journal of Organic Chemistry 2013, nr 31 (13.09.2013): 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 i Xuefeng Li. "Enantioselective synthesis of trifluoromethyl substituted cyclohexanones via an organocatalytic cascade Michael/aldol reaction". Organic & Biomolecular Chemistry 18, nr 8 (2020): 1607–11. http://dx.doi.org/10.1039/d0ob00004c.

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19

Feigenbaum, Alexandre, Yves Fort, Jean Pierre Pete i Denise Scholler. "Photochemical cyclization of 2-alkyl-3-aryl-2-cyclohexenones and 2-alkoxy-3-aryl-2-cyclohexenones". Journal of Organic Chemistry 51, nr 23 (listopad 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 i Jian-Bin Chao. "Palladium-Catalyzed Regioselective Coupling Cyclohexenone into Indoles: Atom-Economic Synthesis of β-Indolyl Cyclohexenones and Derivatization Applications". Organic Letters 22, nr 12 (9.06.2020): 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 i Ning Jiao. "A highly efficient metal-free approach to meta- and multiple-substituted phenols via a simple oxidation of cyclohexenones". Green Chemistry 18, nr 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, i 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, nr 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 i Renhua Liu. "Reaction-activated palladium catalyst for dehydrogenation of substituted cyclohexanones to phenols and H2 without oxidants and hydrogen acceptors". Chemical Science 6, nr 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 i Tianlin Ma. "Catalytic dehydrogenative aromatization of cyclohexanones and cyclohexenones". Organic & Biomolecular Chemistry 16, nr 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 i Alessandro Sega. "The crystal structure and stereochemistry of 2-acetyl-3,5,6-trihydroxy-5,6-dimethyl-2-cyclohexenones". Canadian Journal of Chemistry 66, nr 2 (1.02.1988): 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 i Marcello Nicoletti. "Cyclohexanones from Mimulus glabratus and M. luteus". Natural Product Communications 4, nr 12 (grudzień 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 i Dipakranjan Mal. "Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins". Beilstein Journal of Organic Chemistry 12 (16.03.2016): 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 i Yasuhiko Sawaki. "Regioselective Photocyclodimerization of Cyclohexenones Intercalated on Clay Layers". Chemistry Letters 21, nr 8 (sierpień 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 i Daniel A. Harki. "Bicyclic Cyclohexenones as Inhibitors of NF-κB Signaling". ACS Medicinal Chemistry Letters 3, nr 6 (11.05.2012): 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 i Sangho Koo. "Highly Efficient Synthesis of Methyl-Substituted Conjugate Cyclohexenones". Journal of Organic Chemistry 62, nr 26 (grudzień 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 i Xin-Sheng Yao. "Cyclohexenones and isocoumarins from an endophytic fungus ofSarcosomataceaesp." Journal of Asian Natural Products Research 17, nr 5 (4.05.2015): 550–58. http://dx.doi.org/10.1080/10286020.2015.1043904.

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32

Kraus, George, i Junwon Kim. "A Direct Preparation of 6-Methylene-2-cyclohexenones". Synthesis 2004, nr 11 (22.07.2004): 1737–38. http://dx.doi.org/10.1055/s-2004-829162.

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33

Barluenga, J., M. Suero, R. De la Campa i J. Flórez. "Synthesis of Chiral Cyclohexenones Using a Multicomponent Reaction". Synfacts 2011, nr 02 (19.01.2011): 0179. http://dx.doi.org/10.1055/s-0030-1259345.

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34

Houjeiry, Tania I., Sarah L. Poe i D. Tyler McQuade. "Synthesis of Optically Active 4-Substituted 2-Cyclohexenones". Organic Letters 14, nr 17 (17.08.2012): 4394–97. http://dx.doi.org/10.1021/ol301874x.

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35

MIYAOKA, H., S. SAGAWA, T. INOUE, H. NAGAOKA i Y. YAMADA. "ChemInform Abstract: Efficient Synthesis of Optically Active Cyclohexenones." ChemInform 25, nr 37 (19.08.2010): no. http://dx.doi.org/10.1002/chin.199437030.

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36

Meister, Anne C., Paul E. Sauter i Stefan Braese. "ChemInform Abstract: A Stereoselective Approach to Functionalized Cyclohexenones." ChemInform 45, nr 12 (6.03.2014): 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 i 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, nr 4 (27.12.2018): 715–19. http://dx.doi.org/10.1002/ejoc.201801301.

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38

Ayer, William A., Türkan Gökdemir, Shichang Miao i Latchezar S. Trifonov. "Leptosphaerones A and B, New Cyclohexenones from Leptosphaeria herpotrichoides". Journal of Natural Products 56, nr 9 (wrzesień 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 i D. Díez. "Tandem catalysis for the synthesis of 2-alkylidene cyclohexenones". Tetrahedron 67, nr 43 (październik 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 i Léon Ghosez. "A versatile method of synthesis of anilines and cyclohexenones". Tetrahedron Letters 28, nr 4 (styczeń 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 i Moisés Romero-Ortega. "Synthesis of 3-substituted 2-cyclohexenones through umpoled functionalization". Tetrahedron Letters 58, nr 33 (sierpień 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 i Karl Anker Jørgensen. "A simple asymmetric organocatalytic approach to optically active cyclohexenones". Chem. Commun., nr 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, nr 41 (21.08.2010): no. http://dx.doi.org/10.1002/chin.199241112.

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44

ASAOKA, Morio, i Hisashi TAKEI. "The chemistry of (R)- and (S)-5-trimethylsilyl-2-cyclohexenones." Journal of Synthetic Organic Chemistry, Japan 48, nr 3 (1990): 216–28. http://dx.doi.org/10.5059/yukigoseikyokaishi.48.216.

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Chênevert, Robert, i Daniel Chamberland. "INFLUENCE OF CYCLODEXTRINS ON THE SODIUM BOROHYDRIDE REDUCTION OF CYCLOHEXENONES". Chemistry Letters 14, nr 8 (5.08.1985): 1117–18. http://dx.doi.org/10.1246/cl.1985.1117.

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Chêneverst, Robert, i Guy Ampleman. "SODIUM BOROHYDRIDE REDUCTION OF CYCLOHEXENONES IN THE PRESENCE OF AMYLOSE". Chemistry Letters 14, nr 10 (5.10.1985): 1489–90. http://dx.doi.org/10.1246/cl.1985.1489.

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Bracher, Franz, i André Gehring. "A Convenient Conversion of Substituted Cyclohexenones into Aryl Methyl Ketones". Synthesis 44, nr 15 (29.06.2012): 2441–47. http://dx.doi.org/10.1055/s-0032-1316560.

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Al-Bogami, Abdullah S., Hamad Z. Alkhathlan i Tamer S. Saleh. "Microwave Enhanced Green Synthesis of 2-Pyrazolines, Isoxazolines and Cyclohexenones". Asian Journal of Chemistry 25, nr 11 (2013): 6427–33. http://dx.doi.org/10.14233/ajchem.2013.15070.

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Taber, Douglass F., Kazuo Kanai, Qin Jiang i Gina Bui. "Enantiomerically Pure Cyclohexenones by Fe-Mediated Carbonylation of Alkenyl Cyclopropanes". Journal of the American Chemical Society 122, nr 28 (lipiec 2000): 6807–8. http://dx.doi.org/10.1021/ja994155m.

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Asaoka, Morio, Toshiaki Aida, Syuzo Sonoda i Hisashi Takei. "Enantioselective routes to 2,5-disubstituted- and 4-substituted-2-cyclohexenones". Tetrahedron Letters 30, nr 50 (1989): 7075–78. http://dx.doi.org/10.1016/s0040-4039(01)93427-6.

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