REARRANGEMENTS OF SILYL-SUBSTITUTED AND STANNYL-SUBSTITUTED DIALLYL ETHERS - COMPETITION BETWEEN THE ALLYL-VINYL ETHER REARRANGEMENT AND THE [2,3] WITTIG SIGMATROPIC REARRANGEMENT

Authors
MITCHELL TN GIESSELMANN F KWETKAT K
Citation
Tn. Mitchell et al., REARRANGEMENTS OF SILYL-SUBSTITUTED AND STANNYL-SUBSTITUTED DIALLYL ETHERS - COMPETITION BETWEEN THE ALLYL-VINYL ETHER REARRANGEMENT AND THE [2,3] WITTIG SIGMATROPIC REARRANGEMENT, Journal of organometallic chemistry, 492(2), 1995, pp. 191-197
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Journal of organometallic chemistry → ACNP
ISSN journal
0022328X
Volume
492
Issue
2
Year of publication
1995
Pages
191 - 197
Database
ISI
SICI code
0022-328X(1995)492:2<191:ROSASD>2.0.ZU;2-I
Abstract
Diallyl ethers containing two trimethylstannyl moieties or one triorga nostannyl and one trimethylsilyl moiety attached to the olefinic carbo n atoms of one allyl group can undergo either an allyl-vinyl ether rea rrangement or a [2,3] Wittig sigmatropic rearrangement when treated wi th a strong non-nucleophilic base. While the use of lithium diisopropy lamide favours the Wittig rearrangement, lithium diethylamide can shif t the course of reaction towards the allyl-vinyl ether rearrangement.