ChemInform Abstract: Phenyl‐Substituted Vinylstannanes: Synthesis and Reactivity in Electrophilic Substitution Reactions.

Abstract

Phenyl-Substituted Vinylstannanes: Synthesis and Reactivity in Electrophilic Substitution Reactions.-Three different methods, Grignard coupling, AIBN-catalyzed hydrostannylation and Pd(0)-catalyzed hydrostannylation, are employed to prepare the seven title compounds (III)-(VI), (IX), and (XI). The relative reactivity of these compounds to protodestannylation is interpreted on the basis of the electronic and steric effects of the phenyl substituents. The stereochemistry of destannylation results in retention of configuration for the compounds (III), (IV), (IX) and ( XIa), consistent with an SE2 mechanism, while compound (XIb) reacts via an allenol mechanism to yield an E/Z product (ratio 1:1). -(COCHRAN, J. C.; PHILLIPS, H. K.; TOM, S.; HURD, A. R.; BRONK, B. S.; Organometallics 13 (1994) 3, 947-953; Dep. Chem., Colgate Univ., Hamilton, NY 13346, USA; EN)