Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems

Authors
Braverman, S Zafrani, Y Gottlieb, HE
Citation
S. Braverman et al., Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems, TETRAHEDR L, 41(15), 2000, pp. 2675-2678
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
15
Year of publication
2000
Pages
2675 - 2678
Database
ISI
SICI code
0040-4039(20000408)41:15<2675:TRCAAO>2.0.ZU;2-N
Abstract
The reactivity of some novel pi-conjugated bis-propargylic sulfides, sulfox ides and sulfones under basic conditions has been investigated. These compo unds undergo isomerization to the corresponding diallenes, followed by a ta ndem cyclization and aromatization of the latter via a diradical intermedia te. Surprisingly, we have found that the rate of the cyclization step was i ndependent of the nature of the bridging functionality. (C) 2000 Elsevier S cience Ltd. All rights reserved.