Synthesis of conjugated diallenes by double [2,3]-sigmatropic rearrangement of conjugated diyne trichloromethanesulfenates

Authors
Raj, CP Braverman, S
Citation
Cp. Raj et S. Braverman, Synthesis of conjugated diallenes by double [2,3]-sigmatropic rearrangement of conjugated diyne trichloromethanesulfenates, SYN COMMUN, 29(15), 1999, pp. 2629-2637
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
15
Year of publication
1999
Pages
2629 - 2637
Database
ISI
SICI code
0039-7911(1999)29:15<2629:SOCDBD>2.0.ZU;2-9
Abstract
The preparation of several 2,4-diyne-1,6-diols and their esterification wit h trichloromethanesulfenyl chloride is described. The thus generated bis-pr opargylic trichloromethanesulfenates undergo spontaneous double [2,3]-sigma tropic rearrangement which leads to the formation of conjugated diallenic t richloromethyl sulfoxides in good to excellent yields.