Base catalyzed [2,3]-sigmatropic rearrangements of propargylic sulfonium and selenonium salts

Authors
Braverman, S Zafrani, Y Rahimipour, S
Citation
S. Braverman et al., Base catalyzed [2,3]-sigmatropic rearrangements of propargylic sulfonium and selenonium salts, TETRAHEDR L, 42(15), 2001, pp. 2911-2914
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
15
Year of publication
2001
Pages
2911 - 2914
Database
ISI
SICI code
0040-4039(20010409)42:15<2911:BC[ROP>2.0.ZU;2-5
Abstract
The synthesis and reactivity of bis-gamma -substituted and unsubstituted pr opargylic sulfonium and selenonium salts under various basic conditions hav e been investigated. While the former compounds reacted only by [2,3]-sigma tropic rearrangement of the corresponding sulfur ylides, the latter salts e xhibited a wider range of reactivity and showed potent DNA-cleaving propert ies. (C) 2001 Published by Elsevier Science Ltd.