1,5-HYDRIDE SHIFT IN THE ALUMINUM-CHLORIDE PROMOTED ALLYLSILYLATION OF 5-SILYL-1-ALKENES

Authors
CHOI GM YOO BR LEE HJ LEE KB JUNG IN
Citation
Gm. Choi et al., 1,5-HYDRIDE SHIFT IN THE ALUMINUM-CHLORIDE PROMOTED ALLYLSILYLATION OF 5-SILYL-1-ALKENES, Organometallics, 17(12), 1998, pp. 2409-2413
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Organometallics → ACNP
ISSN journal
02767333
Volume
17
Issue
12
Year of publication
1998
Pages
2409 - 2413
Database
ISI
SICI code
0276-7333(1998)17:12<2409:1SITAP>2.0.ZU;2-V
Abstract
Linear 4-alkyl-5-silyl-1-alkenes 1a-c react with allylsilanes 2a,b in the presence of aluminum chloride catalyst at 40 degrees C to give unu sual allylsilylation products 3a-d derived from an intramolecular sily l group rearrangement in 23-57% yield. The reaction of cyclic 1-allyl- 2-(trimethylsilyl)cycloalkanes 1d,e with 2 gave the silyl-rearranged i somers of 1 in addition to the allylsilylation products 3e,f. The resu lts are consistent with silylenium ion formation and a 1,5-hydride shi ft in the allylsilylation and isomerization.