Some Observations on the Stereochemical and Regiochemical Outcome of Hydrostannylation of Substituted Propargyl Alcohols

Article abstract of DOI:10.1021/jo00239a025

A regio- and stereocontrolled hydrostanyllation of substituted propargyl alcohols and derivatives has been performed.Tri-n-butylstannyl hydride reacts with different substituted propargyl alcohols to give a mixture of Z/E isomers of vinylstannane with the stannyl moiety bonded to the carbon closest to the OH or OR group.A careful study of the reaction conditions allowed the preparation and isolation of pure Z isomer for a wide set of compounds.The reaction products are unstable under the conditions of preparation.An outline of the possible mechanism of the reaction is described.