Journal of the Chemical Society. Perkin transactions II p. 1893 - 1898 (1990)
Update date:2022-08-16
Topics:
Jackson, Lorraine B.
Waring, Anthony J.
4-Benzoyl-4-methylcyclohexa-2,5-dienone is known as one of the few relatively stable 4-acylcyclohexa-2,5-dienones.In attempts to achieve dienone-phenol rearrangements with acyl migration it has been treated with Lewis acids and with non-nucleophilic acids in non-polar solvents.In each case rapid acil migration occurs to give 4-methylphenyl benzoate by a retro-Fries rearrangement, along with some cleavage to the phenol.The benzoyl group can be trapped by another phenol, and the mechanism is formulated as a dissociation-recombination process with significant leakage of the 4-methylphenol and benzoyl cation.The reaction is compared with the Fries/retro-Fries equilibrium which has been induced between phenyl esters and 2- and 4-acyl phenols.Observations are made on the photochemical Fries rearrangement of 4-methylphenyl acetate, which has been suggested to proceed via 4-acetyl-4-methylcyclohexa-2,5-dienone, and of 4-methylphenyl benzoate.
View MoreGolden Union Agrochemical Import and Export Co., Ltd.
Contact:86-755-23910527
Address:Room 1106, Tower 3A, Excellence Century Center, Futian District, Shenzhen, China
Contact:17316303296
Address:240 Amboy Ave
Shanghai Sinofluoro Scientific Co., Ltd
Contact:+86-21-64279360
Address:Room 1006,Building 3,#58 East Xinjian Road, Shanghai ,201100,China,
Frapp's Chemical (NFTZ) Co.,Ltd
Contact:+86-576-86137892
Address:General Chamber of Commercial Building, 159 Wanchang Middle Road, Wenling, Zhejiang, China
Cerametek Materials（ShenZhen）Co., Ltd.
Contact:+86-755-2324.2554
Address:A3-#9, YongChuan Street, Suite 501
Doi:10.1007/BF00531496
(1992)Doi:10.1016/0025-5408(93)90054-H
(1993)Doi:10.1016/S0022-328X(00)90477-7
(1972)Doi:10.1002/anie.201403659
(2014)Doi:10.1021/jo990722c
(1999)Doi:10.1007/BF02251631
(1999)
