Radical Addition of tert-Butyl Hypochlorite to Conjugated Enynes

M Poutsma, P Ibarbia

Index: Poutsma,M.L.; Ibarbia,P.A. Journal of Organic Chemistry, 1970 , vol. 35, p. 4038 - 4047

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Citation Number: 13

Abstract

Radical addition of tert-butyl hypochlorite to 1-buten-3-yne (15) proceeds by competitive olefinic attack to give 1, 2 and 1, 4 adducts (16 and 17) and acetylenic attack to give a 4, 3 adduct (19) which suffers rapid secondary electrophilic chlorination to form aldehyde 18; the former pathway is preferred by a factor of 4 at 25'. Products from the four monomethyl homologs (6, 12, 21, and 29) have also been determined and correlated with the ...