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 

机构地区：[1]Peking Univ, Dept Chem, Beijing 100871, Peoples R China [2]Chinese Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong

出　　处：《Chinese Chemical Letters》1998年第10期899-902,共4页中国化学快报（英文版）

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.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.

关 键 词：C-C bond scission phenolic hydroxy participation 4-hydroxyacetophenones indanols ethylene ketals 

分 类 号：O621[理学—有机化学]