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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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Angara et al. (1991) studied this question.
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