Highly selective trapping of unsymmetrical pentadienyl anions by silicon and tin electrophiles. Marked contrast between kinetic and thermodynamic control of product …

…, Y Nishigaichi, K Maruyama

Index: Naruta, Yoshinori; Nishigaichi, Yutaka; Maruyama, Kazuhiro Journal of Organic Chemistry, 1991 , vol. 56, # 6 p. 2011 - 2017

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Citation Number: 21

Abstract

The nucleophilic reaction of lithium and potassium salts of five pentadienyl anions bearing sterically and/or coordinatively different groups at their unsymmetrical 2-position toward Me, SiCl and Me3SnBr is described. When the anion of the potassium salt was trapped by Me3SiC1, Q-4-substituted-pentenyLsilanes were obtained with high selectivity (87-100%). The lithium salt, however, gave a mixture of (E)-and (2)-4-substituted-pentadienylsilanes. ...