Journal of the American Chemical Society

Positive halogen compounds. VII. intramolecular chlorinations with long chain hypochlorites

C Walling, A Padwa

Index: Walling,C.; Padwa,A. Journal of the American Chemical Society, 1963 , vol. 85, p. 1597 - 1601

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Citation Number: 90

Abstract

The light induced radical chain decomposition of t-hypochlorites with side chains of three carbons or longer has been shown to occur largely via an intramolecular path (1, b-shift of hydrogen) to give 6-chloroalcohols in yields of 1540% plus in some cases small quantities of e-chloroalcohols. The competition with@-scission of the intermediate alkoxy radicals is concentration independent, and the intramolecular reaction is important even in reactive ...