Rapid [3,3] sigmatropic rearrangements of allylic thiono chloroformates

Authors
Zaim, O
Citation
O. Zaim, Rapid [3,3] sigmatropic rearrangements of allylic thiono chloroformates, TETRAHEDR L, 40(46), 1999, pp. 8059-8062
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
46
Year of publication
1999
Pages
8059 - 8062
Database
ISI
SICI code
0040-4039(19991112)40:46<8059:R[SROA>2.0.ZU;2-F
Abstract
Treatment of allylic alcohols with thiophosgene and pyridine gives thiolo c hloroformates directly at room temperature, presumably via very rapid [3,3] sigmatropic rearrangements of thiono chloroformates. Synthesis of allyl th iono chloroformate from allyl alcohol, sodium hydride and thiophosgene at l ow temperature and warming up to room temperature supports this finding. (C ) 1999 Elsevier Science Ltd. All rights reserved.