Tetrahedron letters

Directed ortho metalation of silyloxybenzamides. Anion induced 0→ C silicon rearrangement

RJ Billedau, MP Sibi, V Snieckus

Index: Billedeau, R.J.; Sibi, M.P.; Snieckus, V. Tetrahedron Letters, 1983 , vol. 24, # 42 p. 4515 - 4518

Full Text: HTML

Citation Number: 24

Abstract

Metal-halogen exchange of bromo-substituted trialkylsilyl phenols, to a less extent thiophenols, but not anilines, A,+ 5 triggers an anionic 0+ C 1, 3-silyl rearrangement to produce corresponding aromatic ring silylated derivatives A (S&em&). I Evidence from crossover experiments onA (X= 0) indicates an intramolecular mechanism for oa-bromo and an intermolecular pathway for the corresponding para-bromo trialkylphenoxysilanes. 2 We ...