1-NAPHTHYLMAGNESIUM BROMIDE (703-55-9) 's Synthetic route

1,2-Silyl migration in 1-halonaphthalenes catalyzed by I₂

Shimizu, Tomomi  Morisako, Shogo  Yamamoto, Yohsuke  Kawachi, Atsushi

1-Halo-8-hydrosilylnaphthalenes undergo 1,2-silyl migration to form 1-halo-7-silylnaphthalenes. The influence of the substituents on the silicon atom, the solvent effect, and the D-labeling experiments are investigated. The migration process may include four steps: (a) generation of acid (HI) by the reaction of the hydrosilane with I₂, (b) protonation of the naphthalene ring, (c) silyl group migration in the protonated intermediate, and (d) deprotonation of the naphthalene ring.