Trialkylborane as an initiator and terminator of free radical reactions. Facile routes to boron enolates via. ALPHA.-carbonyl radicals and aldol reaction of boron …

K Nozaki, K Oshima, K Utimoto

Index: Nozaki, Kyoko; Oshima, Koichiro; Utimoto, Kiitiro Bulletin of the Chemical Society of Japan, 1991 , vol. 64, # 2 p. 403 - 409

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Citation Number: 111

Abstract

A variety of trialkylborane-induced reactions were examined for the preparation of the α- carbonyl radicals:(1) addition of alkyl radical to methyl vinyl ketone,(2) reduction of α-halo ketone, and (3) intramolecular radical addition to α, β-unsaturated carbonyl moiety. Trialkylborane reacted with α-carbonyl radicals to give boron enolates. The resulting boron enolates were efficiently trapped by carbonyl compounds to give β-hydroxy ketones in ...

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