Further Report on A Novel Scission of Alkyl Carbonyl C-C Bond by Substituted 4-Hydroxyacetophenones

作     者：Wang, J Tang, HT Zhang, P Mak, TCW Zhang, ZY 

作者机构：Peking Univ Dept Chem Beijing 100871 Peoples R China Chinese Univ Hong Kong Dept Chem Hong Kong Hong Kong 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：1998年第9卷第10期

页      面：899-902页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

主　　题：C-C bond scission phenolic hydroxy participation 4-hydroxyacetophenones indanols ethylene ketals 

摘      要：3-Methoxy-, 3, 5-dimethoxy-, and 3-phenyl-4-hydroxyacetophenones suffered alkyl carbonyl C-C bond scission to yield 4-hydroxybenzoate esters and 4-isopropenylphenols under standard conditions of ethylene ketal formation; the latter underwent in situ dimerization, cyclization, and rearrangement to give substituted indanols. The isopropenylphenol derived from 3,5-ditertbutyl-4-hydroxyacetophenone did not dimerize but condensed with its precursor to yield a substituted diphenylpropanone. 3-nitro-, 3,5-dinitro-, and 3,5-dibromo-4-hydroxyacetophenones on the other hand reacted normally to give ethylene ketals in good yields.