Abstract

α-Iodoenones and α-bromoenones are formed from secondary alkynols by the use of the appropriate N-halosuccinimide and a catalytic amount of certain Lewis acids. For example, 3-hexyn-2-ol ( 1 ) was converted to (Z)-4-iodo-4-hexen-3-one ( 2 ) in 85–95% yields with an equimolar quantity of NIS and tenth molar (hydroxy (toxyloxy) iodo) benzene ( 3 ) in methanol or 1-methyl-2-pyrrolididone

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