Studies on the Mechanism of Reactions of Substituted Acetophenones with Dibromocarbene

Abstract

Abstract: Mechanistic study on the reactions of dibromocarbene with para-substituted ace-tophenones suggests that the reactions proceed via the formation of a twisted carbonyl Ylide intermediate which causes two competitive pathways, i.e., (1) deoxygenation(in the form of losing CO and (2) electrocyclization. Although deoxygenation was observed not to be the major reaction path, it is clear that the extent of this reaction is increased substantively with respect to electron-donating substituents. This phenomena is rationalized based mainly on the electronic effect of substituents on each reaction path involved as well as the twisted con-firmation of Ylide intermediate.

Key words: Dibromocarbene, Acetophenone, Deoxygenation, Carbonyl Ylide

CLC Number:

O623

TrendMD:

GU Wen-Xiang, WANG Hong-Xing, HUAN Zhen-Wei  . Studies on the Mechanism of Reactions of Substituted Acetophenones with Dibromocarbene[J]. Chem. J. Chinese Universities, 1999, 20(7): 1068.

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Studies on the Mechanism of Reactions of Substituted Acetophenones with Dibromocarbene

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