Synthesis of α-substituted allyl- and homoallyl-stannanes by selenoxide elimination

Abstract

The α-methyl-, α-phenyl- and α,α-dimethyl-allylstannanes 20–22 have been prepared by oxidative elimination of the corresponding primary selenides 17–19, and were found to be stable with respect to 1,3-migration of the tributyltin moiety in non-polar solvents (t⩽ 100 °C). Homoallylstannanes 32–34 were the major products obtained by oxidative elimination of the secondary selenides 29–31, with mixtures of regioisomers being obtained from the other secondary selenides investigated.