Open Access1,2‐Silyl migration in 1‐halonaphthalenes catalyzed by I 2
Author(s) -
Shimizu Tomomi,
Morisako Shogo,
Yamamoto Yohsuke,
Kawachi Atsushi
Publication year - 2018
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/hc.21434
Subject(s) - chemistry , protonation , silylation , deprotonation , naphthalene , ring (chemistry) , catalysis , medicinal chemistry , solvent , silicon , halo , organic chemistry , ion , physics , quantum mechanics , galaxy
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 I 2 , (b) protonation of the naphthalene ring, (c) silyl group migration in the protonated intermediate, and (d) deprotonation of the naphthalene ring.