Preparation of multisubstituted allenes from allylsilanes

M Ogasawara, Y Ge, K Uetake, L Fan…

Index: Ogasawara, Masamichi; Ge, Yonghui; Uetake, Koichi; Fan, Liyan; Takahashi, Tamotsu Journal of Organic Chemistry, 2005 , vol. 70, # 10 p. 3871 - 3876

Full Text: HTML

Citation Number: 24

Abstract

A three-step route of converting allylsilanes to functionalized allenes was developed. Thermal decomposition of 1, 1-dibromo-2-(silylmethyl) cyclopropanes, which were quantitatively prepared by treatment of allylsilane derivatives with CHBr3/KO t Bu, afforded substituted 2-bromo-1, 3-butadienes with elimination of bromosilanes. The Pd-catalyzed reaction of the bromodienes with soft nucleophiles gave the allene derivatives. Previously ...