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Journal articles on the topic 'Dienone'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Hartshorn, MP, MC Judd, RJ Martyn, WT Robinson, GJ Wright, and RW Vannoort. "Reactions of 3,4,5-Trimethylbiphenyl and 2,3,4-Trimethylbiphenyl With Nitrogen Dioxide." Australian Journal of Chemistry 43, no. 9 (1990): 1519. http://dx.doi.org/10.1071/ch9901519.

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Reaction of 3,4,5-trimethylbiphenyl (1) with nitrogen dioxide gives four mononitro compounds (3)-(6) and three dinitro compounds (7)-(9). Similar reaction of 2,3,4-trimethylbiphenyl (2) gives three nitroaromatic compounds (11)-(13), three nitrate esters (14)-(16), and two nitro dienones (17) and (18). Dinitro dienone (17) rearranges in solution to give the corresponding hydroxy nitro dienone (19). The differences between the two sets of products are discussed, and an addition-elimination mechanism is proposed for the mode of formation of the nitro dienones (17) and (18). X-Ray crystal structur

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2

Fischer, Alfred, George N. Henderson, and S. Sankararaman. "Preparation of and addition of carbanions to 6-methyl-6-nitrocyclohexa-2,4-dienones." Canadian Journal of Chemistry 67, no. 7 (1989): 1244–46. http://dx.doi.org/10.1139/v89-189.

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Nitration of 2-methylphenols with nitric acid and trifluoroacetic anhydride in ether at −78 °C gives 6-methyl-6-nitrocyclo-hexa-2,4-dienones that can be isolated. Carbanions add to 5,6-dimethyl-6-nitrocyclohexa-2,4-dienone to give the 5-substituted 2,3-dimethyl-2-nitrocyclohex-3-enone anion, which, with additional carbanion, gives the 5-substituted 2,3-dimethylphenoxide anion by elimination of nitrous acid. Keywords: nitration, dienone, addition, carbanion, nucleophilic.

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3

Blunt, JW, MP Hartshorn, RG Jensen, AG Waller, and GJ Wright. "15N Labeling Studies of the Reactions of 4-t-Butyl-2,6-dimethyl-4-nitrocyclohexa-2,5-dienone and 2,4-Di-t-butyl-6-methyl-4-nitrocyclohexa-2,5-dienone With Nitrogen-Dioxide; the Mechanism of Formation of 2,5,6-Trinitrocyclohex-3-enones." Australian Journal of Chemistry 42, no. 5 (1989): 675. http://dx.doi.org/10.1071/ch9890675.

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Reaction of the 15N-labelled 4-nitro dienone (15b) with nitrogen dioxide in benzene gives the 2,5,6-trinitrocyclohex-3-enones (19), (20), (22) and (24) with retention of some 15N-label at C6. Similar reaction of 15N-labelled 4-nitro dienone (18b) gives the 2,5,6-trinitrocyclohex-3-enones (30), (31), (34) and (38), and the 2-hydroxy-5,6- dinitrocyclohex-3-enones (33) and (37) all with retention of some 15N-label at C6. These results are rationalized in terms of 2,5-addition of nitrogen dioxide to corresponding intermediate 6-nitro dienones (27) and (40).

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4

Goodyear, Gary, and Anthony J. Waring. "Dienone–phenol rearrangements of 3-acylcyclohexa-2,5-dienones: kinetics and mechanism." J. Chem. Soc., Perkin Trans. 2, no. 1 (1990): 103–7. http://dx.doi.org/10.1039/p29900000103.

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5

Gray, MJ, MP Hartshorn, WT Robinson, and J. Vaughan. "Substituent Effects in the Reactions of Some Polysubstituted 4-Hydroxy-4-methylcyclohexa-2,5-Dienones With Hydroxide Ion; X-Ray Structure Analyses of 2,5,6-Tribromo-3,4-dihydroxy-4-methylcyclohexa-2,5-dienone and 3,4-Dibromo-5-methyl-5-nitroacetylfuran-2(5H)-one." Australian Journal of Chemistry 40, no. 10 (1987): 1769. http://dx.doi.org/10.1071/ch9871769.

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Reactions of the 2,3,5,6-substituted 4-hydroxy-4-methylcyclohexa-2,5-dienones (6a), (6b), (7a) and (7b) with hydroxide ion give 3,4-dihydroxy dienones (9a), (9b), (10) and (11). In contrast, hydroxide ion treatment of the substituted nitro dienone (8), followed by acidification, gives the substituted furan-2(5H)-one (12). The effect of substituents on the course of the reactions is discussed. X-ray structure determinations for compounds (9a) and (12) are reported.

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6

Xia, Zilei, Jiadong Hu, Zhigao Shen, Qizheng Yao, and Weiqing Xie. "Re2O7catalyzed dienone-phenol rearrangement." RSC Advances 5, no. 48 (2015): 38499–502. http://dx.doi.org/10.1039/c5ra04931h.

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7

Mondon, Martine, Norbert Boeker, and Jean-Pierre Gesson. "Cycloaddition of Ketene Acetals with 4-Bromo-6-spiroepoxycyclohexa-2,4-dienone." Journal of Chemical Research 23, no. 8 (1999): 484–85. http://dx.doi.org/10.1177/174751989902300815.

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4-Bromo-6-spiroepoxycyclohexa-2,4-dienone reacts as a diene in an inverse electron-demand reaction with 1-ethoxy-3-methoxy-1-trimethylsilyloxybuta-1,3-diene but as a dienophile with 1-ethoxy-3-methylene-4-(ethoxy trimethylsilyloxymethylene)-1-cyclohexene.

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8

Hartshorn, MP, MC Judd, RW Vannoort, and GJ Wright. "The Nitration of 4-Methylphenol, 3,4-Dimethylphenol and 3,4,5-Trimethylphenol With Nitrogen Dioxide." Australian Journal of Chemistry 42, no. 5 (1989): 689. http://dx.doi.org/10.1071/ch9890689.

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Reaction of 4-methylphenol (la) with excess nitrogen dioxide in either benzene or dichloromethane gives the 4-nitro dienone (2a) and the 2,6-dinitrophenol (5). Similar reactions of 3,4-dimethylphenol (Ib) yields the 4-nitro dienone (2b), the 2,6-dinitrophenol (8) and the 4-hydroxy 2,6-dinitro dienone (9), while reaction of 3,4,5-trimethylphenol (1c) gives the 4-nitro dienone (2c), the 2,4-dinitro dienone (11) and the 2,4,6-trinitro dienone (12a). The reaction pathways by which these products are formed are described and the results of reactions of postulated intermediates with nitrogen dioxide

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9

Cambie, RC, HM Craw, CEF Rickard, et al. "An Oxidative Decarboxylation of 7-Oxopodocarpic Acid Derivatives." Australian Journal of Chemistry 43, no. 5 (1990): 883. http://dx.doi.org/10.1071/ch9900883.

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Treatment of the 7-oxopodocarpic acid derivatives (1) and (3) with 2,3-dichloro-5,6-dicyanobenzoquinone affords the conjugated dienones (5) and (6) directly. The latter compounds have potential as optically active relays for the synthesis of 3-oxygenated diterpenoids . The stereochemistry of an epoxide (7) formed from the dienone (5) has been confirmed by X-ray crystallography.

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10

O'Neal, Charissa, Edward V. Sargent, and Walter Bagdon. "Acute Toxicologic Evaluation of Dienone." Journal of the American College of Toxicology 1, no. 3 (1992): 186–87. http://dx.doi.org/10.1177/109158189200100332.

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11

Hartshorn, MP, RJ Martyn, WT Robinson, KH Sutton, J. Vaughan, and JM White. "Reactions of 4-Methyl-2,6-diphenylphenol and 4-Nitro-2,6-diphenylphenol with Nitrogen Dioxide." Australian Journal of Chemistry 38, no. 11 (1985): 1613. http://dx.doi.org/10.1071/ch9851613.

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Reaction of 4-methyl-2,6-diphenylphenol (11a) with nitrogen dioxide in benzene solution gives the polysubstituted cyclohex-2-enones (14), (15), (16), (17) and (18) via the 4-nitro dienone (13). The reversibility of the 4-nitro dienone (13)/4-hydroxy dienone (19) conversion under these reaction conditions is demonstrated. Reaction of 4-nitro-2,6-diphenylphenol (11b) with nitrogen dioxide in benzene solution gives the C2-epimeric 2,6-dihydroxy-4,5-dinitrocyclohex-3- enones (32) and (33) via the 6-nitro-6-phenyl dienone (12b). X-ray crystal structure analyses are reported for compounds (14), (15)

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12

Teeyapant, R., H. J. Woerdenbag, P. Kreis, et al. "Antibiotic and Cytotoxic Activity of Brominated Compounds from the Marine Sponge Verongia aerophoba." Zeitschrift für Naturforschung C 48, no. 11-12 (1993): 939–45. http://dx.doi.org/10.1515/znc-1993-11-1218.

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Abstract Analysis of the marine sponge Verongia aerophoba from the Canary Islands afforded eight brominated secondary metabolites including the small molecular weight compounds aeroplysinin-1 (5) and the dienone (7) which were previously shown to arise by enzymatically catalyzed degradation of aerophobin-2 (4) and isofistularin-3 (1) following breakdown of the cellular compartmentation of the sponge. All compounds were identified from their NMR and mass spectra. Aeroplysinin-1 as well as dienone which arise from isofistularin-3 or aeropho bin-2 by biotransformation within the sponge showed a

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13

Krasnaya, Zh A. "Dienone ⇆ 2H-pyran valence isomerization. (Review)." Chemistry of Heterocyclic Compounds 35, no. 11 (1999): 1255–71. http://dx.doi.org/10.1007/bf02251992.

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14

Bazzaro, Martina, and Stig Linder. "Dienone Compounds: Targets and Pharmacological Responses." Journal of Medicinal Chemistry 63, no. 24 (2020): 15075–93. http://dx.doi.org/10.1021/acs.jmedchem.0c00812.

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15

Mallick, Rajendra K., Shubham Dutta, Rajeshwer Vanjari, Arnaud Voituriez, and Akhila K. Sahoo. "Thioarylative Radical Cyclization of Yne-Dienone." Journal of Organic Chemistry 84, no. 16 (2019): 10509–17. http://dx.doi.org/10.1021/acs.joc.9b01445.

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16

Kumar, V. S. Senthil, and Ashwini Nangia. "2,2′-Diselenobis(4,4-diphenylcyclohexa-2,5-dienone)." Acta Crystallographica Section C Crystal Structure Communications 56, no. 1 (2000): 123–24. http://dx.doi.org/10.1107/s0108270199012743.

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17

Xia, Zilei, Jiadong Hu, Zhigao Shen, Qizheng Yao, and Weiqing Xie. "ChemInform Abstract: Re2O7Catalyzed Dienone-Phenol Rearrangement." ChemInform 46, no. 35 (2015): no. http://dx.doi.org/10.1002/chin.201535083.

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18

Pavkovic, S. F., та E. J. Zaluzec. "A tetracarbonyl(η4-dienone)chromium complex". Acta Crystallographica Section C Crystal Structure Communications 45, № 1 (1989): 18–21. http://dx.doi.org/10.1107/s010827018801008x.

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19

Vostrikov, N. S., V. V. Zagitov, and M. S. Miftakhov. "New 11,13-Dienone Analog of Cloprostenol." Russian Journal of Organic Chemistry 55, no. 10 (2019): 1465–68. http://dx.doi.org/10.1134/s1070428019100038.

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20

Deslongchamps, Pierre, André Bélanger, Daniel J. F. Berney, et al. "The total synthesis of (+)-ryanodol. Part I. General strategy and search for a convenient diene for the construction of a key tricyclic intermediate." Canadian Journal of Chemistry 68, no. 1 (1990): 115–26. http://dx.doi.org/10.1139/v90-021.

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This paper reports a retrosynthetic analysis that led to the conception of a synthetic strategy for the construction of ryanodol (2). The preparation of a key diene, i.e., spirolactone dienone 47 (19 → 31 → 33 → 48 → 49 → 52 → 47), and its Diels–Alder reaction with methyl vinyl ketone are reported. Keywords: strategy, synthesis, ryanodol, diterpene.

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21

Vyglazov, O. G., �. N. Manukov, B. G. Udarov, G. N. Bazhina, T. R. Urbanovich, and L. V. Izotova. "2,6,6-Trimethylcyclohepta-2,4-dienone and 3,6,6-trimethylcyclohepta-2,4-dienone ? Components of the turpentine from Pinus sylvestris." Chemistry of Natural Compounds 25, no. 2 (1989): 253–54. http://dx.doi.org/10.1007/bf00598429.

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22

Hartshorn, MP, JA Kennedy, RW Simpson, J. Vaughan, and GJ Wright. "Some Rearrangements of 2,4,6-Tri-t-butyl-4-nitrocyclohexa-2,5-dienone." Australian Journal of Chemistry 38, no. 5 (1985): 735. http://dx.doi.org/10.1071/ch9850735.

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Rearrangement of 2,4,6-tri-t-butyl-4-nitrocyclohexa-2,5-den (20) in benzene gives the 4-hydroxy dienone (21) and the mono-de-t- butylated 1,2-benzoquinone (22). The rearrangement is not affected by the addition of mesitylene , but the phenol-coupling product (26) is formed in the presence of p-cresol, and the nitromethyl phenol (31) is formed when the nitro dienone (20) rearranges in the presence of 2,4,6- trimethylphenol (29). The rearrangements of the nitro dienone (20) in methanol are described.

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23

Jackson, Lorraine B., and Anthony J. Waring. "4-Benzoyl-4-methylcyclohexa-2,5-dienone and its benzoyl substituted derivatives: isolated 4-acylcyclohexa-2,5-dienones." Journal of the Chemical Society, Chemical Communications, no. 13 (1985): 857. http://dx.doi.org/10.1039/c39850000857.

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24

Urech, R. "Synthesis of (±)-Clavularin B." Australian Journal of Chemistry 39, no. 3 (1986): 433. http://dx.doi.org/10.1071/ch9860433.

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(�)- Clavularin B (2b) was prepared from cyclohepta-2,6-dienone (4) via a Michael reaction of the lithium dienolate anion (5a) with the trimethylsilyl -substituted methyl vinyl ketone (11). The structures of the clavularins A and B were thus unambiguously established as cycloheptenone derivatives (2a) and (2b). The Mukaiyama reaction between the silyl dienol ether (5b) and but-3-en-2-one gave 8-acetyl-4- methylbicyclo[3.2.2]nonan-6-one (9).

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25

Gabriel, Frédéric L. P., Andy Heidlberger, Daniel Rentsch, Walter Giger, Klaus Guenther, and Hans-Peter E. Kohler. "A Novel Metabolic Pathway for Degradation of 4-Nonylphenol Environmental Contaminants bySphingomonas xenophagaBayram." Journal of Biological Chemistry 280, no. 16 (2005): 15526–33. http://dx.doi.org/10.1074/jbc.m413446200.

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Several nonylphenol isomers with α-quaternary carbon atoms serve as growth substrates forSphingomonas xenophagaBayram, whereas isomers containing hydrogen atoms at the α-carbon do not (Gabriel, F. L. P., Giger, W., Guenther, K., and Kohler, H.-P. E. (2005)Appl. Environ. Microbiol.71, 1123–1129). Three metabolites of 4-(1-methyloctyl)-phenol were isolated in mg quantities from cultures of strain Bayram supplemented with the growth substrate isomer 4-(1-ethyl-1,4-dimethyl-pentyl)-phenol. They were unequivocally identified as 4-hydroxy-4-(1-methyl-octyl)-cyclohexa-2,5-dienone, 4-hydroxy-4-(1-meth

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26

Kraft, Philip, Samuel Jordi, Natacha Denizot, and Irene Felker. "On the Dienone Motif of Musks: Synthesis and Olfactory Properties of Partially and Fully Hydrogenated Dienone Musks." European Journal of Organic Chemistry 2014, no. 3 (2013): 554–63. http://dx.doi.org/10.1002/ejoc.201301107.

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27

Gordon, JLM, MP Hartshorn, WT Robinson, et al. "The Reactions of Some Substituted 2-Hydroxybenzonitriles With Nitrogen Dioxide: X-Ray Structures of 2-Cyano-t-6-hydroxy-3,4,5,6-tetramethyl-r-4,t-5-dinitrocyclohex- 2-enone, 2-Cyano-3,4,5,6-tetramethyl-r-4,t-5,t-6-trinitrocyclohex-2-enone and 2-Cyano-c-6-h-4,6-dimethyl-r-4,c-5-dinitrocyclohex-2-enone." Australian Journal of Chemistry 43, no. 3 (1990): 579. http://dx.doi.org/10.1071/ch9900579.

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Reaction of 2-hydroxy-3,4,5,6-tetramethylbenzonitrile (1c) with nitrogen dioxide gives predominantly the 4,5,6-trinitrocyclohex-2-enones (9) and (10a,b), with lower yields of the 4-nitro dienone (5a) and the 6-hydroxy-4,5-dinitrocyclohex-2-enone (6). Reaction of 2-hydroxy-3,5-dimethylbenzonitrile (2b) with nitrogen dioxide gave the C4-epimeric 6-hydroxy-4,5-dinitrocyclohex-2-enones (11) and (12). Reaction of 2-hydroxy-3,5,6-trimethyl- benzene-1,4-dicarbonitrile (4) with nitrogen dioxide gave the 4-hydroxy dienone (15) and the 6-hydroxy dienone (16). X-Ray structure determinations are reported

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28

K. Banerjee, Ajoy, and Hector E. Hurtado S. "Acid catalysed novel rearrangement of bicyclic dienone." Tetrahedron 41, no. 15 (1985): 3029–32. http://dx.doi.org/10.1016/s0040-4020(01)96654-2.

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29

Krasnaya, Zh A. "ChemInform Abstract: Dienone⇔2H-Pyran Valence Isomerization." ChemInform 31, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.200034246.

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30

Canesi, Sylvain, Gaëtan Maertens, and Marc-André Ménard. "Catalytic Enantioselective Desymmetrizations of Prochiral Dienone Systems." Synthesis 46, no. 12 (2014): 1573–82. http://dx.doi.org/10.1055/s-0033-1341224.

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31

Mo, De-Juan, Jun Li, and Min-Yi Li. "A New 28-Nor-oleanane Triterpene from Excoecaria agallocha." Natural Product Communications 13, no. 1 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300107.

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A new 28-nor-oleanane triterpene, 28- nor-olean-2α, 3β-dihydroxy-14,17-diene-16-one with a rare cyclohexa-2,5-dienone moiety, together with three known triterpenes, viz.β-amyrin (2), 3α- O - trans -coumaroyl-betulinic acid (3), 3-acetyl-aleuritolic acid (4), were isolated from the twigs of Excoecaria agallocha L.. Their structures were determined by extensive spectroscopic data analysis and comparison with previous literatures (known compounds).

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32

Franck-Neumann, Michel, Philippe Geoffroy, and Dominique Gassmann. "Synthesis of Mono- and Polycyclic Tricarbonyliron Cyclohexa-2,4-dienone Complexes and Phenols from Tosylhydrazones of Acyclic Dienone Complexes." Synlett, no. 12 (2002): 2054–58. http://dx.doi.org/10.1055/s-2002-35598.

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33

Wang, Quanrui, Sereina Riniker, Philip Kraft, et al. "A New Family of Rigid Dienone Musks Challenges the Perceptive Range of the Human Olfactory Receptor OR5AN1." Synlett 31, no. 10 (2020): 972–76. http://dx.doi.org/10.1055/s-0040-1708009.

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A new family of dienone musks was discovered by alkylation of different aldehydes with but-3-en-1-yn-1-yllithium and subsequent domino reaction of a Saucy–Marbet transfer vinylation–Claisen rearrangement with an intramolecular Diels–Alder reaction, and concluding Lewis acid catalyzed double-bond isomerization. The newly synthesized dienone structures possess pleasant musk odors displaying fatty, slightly fruity and green facets. Although the dienone musks were predicted in silico to bind to the OR5AN1 receptor based on QM/MM calculations, they were found to be inactive in the in vitro assay. T

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34

Koşar, Başak, Orhan Büyükgüngör, Çiğdem Albayrak, and Mustafa Odabaşoğlu. "3-Hydroxy-6-[(4-hydroxyphenylamino)methylene]cyclohexa-2,4-dienone and 2-hydroxy-6-[(4-hydroxyphenylamino)methylene]cyclohexa-2,4-dienone." Acta Crystallographica Section C Crystal Structure Communications 60, no. 6 (2004): o458—o460. http://dx.doi.org/10.1107/s0108270104010832.

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35

Jackson, Lorraine B., and Anthony J. Waring. "Synthesis of 4-benzoyl-4-methylcyclohexa-2,5-dienone and its benzoyl substituted derivatives: isolated 4-acylcyclohexa-2,5-dienones." Journal of the Chemical Society, Perkin Transactions 1, no. 7 (1988): 1791. http://dx.doi.org/10.1039/p19880001791.

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36

Hartshorn, MP, AD Roddick, PJ Steel, and GJ Wright. "The Chlorination of 2-t-Butyl-4-chloro-6-methylphenol. Some Reactions of Chlorine and Nitrogen Dioxide With 6-Chlorocyclohexa-2,4-dienones Derived From 2-t-Butyl-4-chloro-6-methylphenol." Australian Journal of Chemistry 45, no. 4 (1992): 721. http://dx.doi.org/10.1071/ch9920721.

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Chlorinations of 2-t-butyl-4-chloro-6-methylphenol(10) and of the mixture of 4,6-dichlorocyclo-hexa-2,ddienones (11) and (12) give the tetrachloro ketones (13)-(15). Reaction of the dichlorocyclohexa-2,4-dienone mixture with nitrogen dioxide gives predominantly dichloro dinitro ketones (17) which rearrange on chromatography to yield the hydroxy dienone (21). X-Ray crystal structures are reported for compounds (13)-(15), (20) and (21).

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37

Brisimitzakis, Angelo C., David I. Schuster, and James M. van der Veen. "Stereochemical assignment by X-ray crystallography to the product of trapping by solvent of the intermediate zwitterion on irradiation of a 2,5-cyclohexadienone." Canadian Journal of Chemistry 63, no. 3 (1985): 685–87. http://dx.doi.org/10.1139/v85-113.

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Ultraviolet irradiation of 4-methyl-4-trichloromethylcyclohexa-2,5-dienone in acidic methanol resulted in the stereospecific generation of a solvent adduct, whose structure has been determined by X-ray crystallography, and whose carbon skeleton can be identified with that of the previously postulated zwitterion intermediate. It is concluded that the photochemical rearrangement of this dienone to the corresponding lumiketone proceeds with inversion of configuration at the migratory carbon.

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38

Černý, Václav, Miloš Buděšínský, Miloš Ryba та František Tureček. "A contribution to peroxy acid oxidation of α,β-unsaturated ketones and linearly conjugated dienones: Reactions in the cholestane series". Collection of Czechoslovak Chemical Communications 53, № 7 (1988): 1549–67. http://dx.doi.org/10.1135/cccc19881549.

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Oxidation with 3-chloroperoxybenzoic acid of s-cis α,β-unsaturated ketones IX, XI and s-trans types X, XII was compared. The s-cis ketones show higher reactivity and furnish a higher yield of the corresponding α,β-epoxy ketones than the s-trans ketones. Products of the Baeyer-Villiger reaction are formed only in low yield. The dienone VI is oxidized predominantly to VII thus violating the rule that linear conjugated dienones are epoxidized at the double bond more distant from the carbonyl group; this result is in accord with the behaviour of s-cis α,β-unsaturated ketones. 1H NMR and 13C NMR da

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39

Rogers, Colin B. "Cycloartenoid dienone acids and lactones from Combretum erythrophyllum." Phytochemistry 49, no. 7 (1998): 2069–76. http://dx.doi.org/10.1016/s0031-9422(98)00414-2.

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40

Schwarzer, Anke, and Edwin Weber. "3,4-Bis(4-bromophenyl)-2,5-diphenylcyclopenta-2,4-dienone." Acta Crystallographica Section E Structure Reports Online 63, no. 10 (2007): o3966. http://dx.doi.org/10.1107/s1600536807035702.

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41

Shujah, Shaukat, Saqib Ali, Zia-ur-Rehman, M. Nawaz Tahir, and Auke Meetsma. "6-[(2,4-Dimethylanilino)methylidene]-2-hydroxycyclohexa-2,4-dienone." Acta Crystallographica Section E Structure Reports Online 69, no. 6 (2013): o871. http://dx.doi.org/10.1107/s1600536813012233.

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42

Hampel, Nathalie, Dorothea Richter, Armin R. Ofial, Herbert Mayr, and Peter Mayer. "4-[4-(Dimethylamino)benzylidene]-2,6-dimethylcyclohexa-2,5-dienone." Acta Crystallographica Section E Structure Reports Online 65, no. 9 (2009): o2102. http://dx.doi.org/10.1107/s1600536809030748.

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43

Shi, Xiaolian, Roberta Day, and Bernard Miiier. "Bromine-induced aromatic alkylation and dienone-phenol rearrangements." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1989): 1166. http://dx.doi.org/10.1039/p19890001166.

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44

Giarrusso, Marilena A., Luke T. Higham, Ulf P. Kreher, et al. "Platform technology for dienone and phenol–formaldehyde architectures." Green Chemistry 10, no. 8 (2008): 842. http://dx.doi.org/10.1039/b802755b.

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45

Kumar, V. S. Senthil, and Ashwini Nangia. "ChemInform Abstract: 2,2′-Diselenobis(4,4-diphenylcyclohexa-2,5-dienone)." ChemInform 31, no. 22 (2010): no. http://dx.doi.org/10.1002/chin.200022032.

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46

Carroll, AR, AS Krauss, and WC Taylor. "Intramolecular Oxidative Coupling of Aromatic Compounds. V. para-para Diphenolic Oxidative Coupling as a Possible Route to the Eupodienone Skeleton." Australian Journal of Chemistry 46, no. 3 (1993): 277. http://dx.doi.org/10.1071/ch9930277.

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Abstract:

The synthesis of (2RS,3RS)-1,4-bis(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dimethylbutan-1-one (9) is described. Diphenolic oxidative coupling of (9) gave the unstable dienone (24), which decomposed in methanol to give what is believed to be the acetal (26). Synthesis of the related diarylbutane (10) was also achieved, but diphenolic coupling gave no useful result. The claimed formation of the bis ( spiro dienone ) (7) on oxidation of 4,4′-(butane-1,4-diyl) bisphenol could not be confirmed.

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47

Fischer, Alfred, George N. Henderson, and Sumit RayMahasay. "ipso Nitration. XXIX. Nitration of substituted 4-methylanisoles and phenols." Canadian Journal of Chemistry 65, no. 6 (1987): 1233–40. http://dx.doi.org/10.1139/v87-209.

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Abstract:

Nitration of 2-chloro-4-methylanisole (1a) in acetic anhydride gives (Z)-4-chloro-3-methoxy-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate (2a), 2-chloro-4-methyl-4-nitrocyclohexa-2,5-dienone (3a), and 2-chloro-4-methyl-6-nitroanisole (4a). Similarly 2-bromo-4-methylanisole (1b) gives (Z)-4-bromo-3-methoxy-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate (2b), 2-bromo-4-methyl-4-nitrocyclohexa-2,5-dienone (3b), and 2-bromo-4-methyl-6-nitroanisole (4b), whereas 4-methyl-2-nitroanisole (1c) gives (Z)-3-methoxy-6-methyl-4,6-dinitrocyclohexa-2,4-dienyl acetate (2c), (Z)-3-methoxy-6-methyl-2,6-dinitrocyc

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48

Gordon, JLM, MP Hartshorn, RJ Martyn, WT Robinson, and GJ Wright. "The Mechanism and Stereochemistry of Chlorination of 2,4-Dichloro-3,,5,6-trimethylphenol and 2,4-Dichloro-3,6-dimethylphenol." Australian Journal of Chemistry 47, no. 2 (1994): 279. http://dx.doi.org/10.1071/ch9940279.

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Abstract:

Electrophilic attack of chlorine on 2,4,6-trichloro-3,5,6-trimethylcyclohexa-2,4-dienone (2a) gives the trans-pentachloro ketones (3a) and (4a), while similar reaction of 2,4,6-trichloro-3,6-dimethylcyclohexa-2,4-dienone (2b) gives the trans- pentachloro ketones (3b) and (4b), resulting from 2,5- and 4,5-addition of chlorine. The probable stereochemistry of chlorine addition in ketones (3b) and (4b) is determined by chlorination of 2,4-dibromo-3,6-dimethylphenol (6). X-Ray crystal structures are reported for compounds (3a,b), (7) and (8).

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49

Cui, Han Feng, Yan Lin, Hao Fan, Li De Yu, and Ping Nan Wan. "Amino Acid Catalyzed Conjugate Addition of Thiol to Dienone." Advanced Materials Research 834-836 (October 2013): 450–53. http://dx.doi.org/10.4028/www.scientific.net/amr.834-836.450.

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50

Sauer, Anne M., William E. Crowe, Gregg Henderson, and Roger A. Laine. "Conformational control of selectivity in the dienone–phenol rearrangement." Tetrahedron Letters 48, no. 37 (2007): 6590–93. http://dx.doi.org/10.1016/j.tetlet.2007.07.001.

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