1,2-BIS-(TRIALKYLSILYL)ETHANES - SYNTHONS FOR VICINAL DICATIONS

Authors
PORTER JM XUAN XY BLACKMAN B HSU D FRY AJ
Citation
Jm. Porter et al., 1,2-BIS-(TRIALKYLSILYL)ETHANES - SYNTHONS FOR VICINAL DICATIONS, Tetrahedron letters, 38(41), 1997, pp. 7147-7150
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
41
Year of publication
1997
Pages
7147 - 7150
Database
ISI
SICI code
0040-4039(1997)38:41<7147:1-SFVD>2.0.ZU;2-O
Abstract
Anodic oxidation of 1,2-bis-(trimethylsilyl)-1,2-diphenylethane in met hanol affords a 65:35 mixture of 1,2-dimethoxy-1,2-diphenylethane (dl: meso = 10:1 and diphenylacetaldehyde dimethylacetal. The results can b e interpreted in terms of a 1,2-diaryl-2-methoxyethyl cation, which ca n undergo either nucleophilic attack by solvent or rearrangement to a 2,2-diaryl-1-methoxyethyl cation. Experiments testing the generality o f the reaction are described. (C) 1997 Elsevier Science Ltd.