Electrophilic Additions to Alkynyl Tosylates. Formation of Vinyl 1,1-(Bis esters) and Related Compounds. X-ray Structure Determination of (E)-1-Chloro-1-(tosyloxy)-3,3-dimethyl-1-butene

Article abstract of DOI:10.1021/jo00232a028

The reaction of alkynyl tosylates, RCCOTs, R=t-Bu, sec-Bu, with a variety of electrophiles, HCl, CF3COOH, CF3SO3H, ArSO3H, and H3O⁺, in CH2Cl2 is reported.Only regio- and stereospecific syn-monoaddition products were observed, yielding vinyl 1,1-(bis esters) and related compounds in good yields.The single-crystal X-ray data of the HCl adduct to t-BuCCOTs is reported.These results and their mechanistic implications are discussed.