A surprising rearrangement of a carbene-ethylene sulfide ylide

Authors
Tae, EL Zhu, ZD Platz, MS
Citation
El. Tae et al., A surprising rearrangement of a carbene-ethylene sulfide ylide, TETRAHEDR L, 40(27), 1999, pp. 4921-4924
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
27
Year of publication
1999
Pages
4921 - 4924
Database
ISI
SICI code
0040-4039(19990702)40:27<4921:ASROAC>2.0.ZU;2-6
Abstract
Photolysis of 2-methoxy-2-methyl-5,5-dipropyl-Delta(3)-1,3,4 oxadiazoline i n methylene chloride produces 4 diazoheptane which can undergo secondary ph otolysis to form dipropylcarbene. Dipropylcarbene reacts with ethylene sulf ide to form a ylide which rearranges to form a vinyl sulfide. Calculations indicate that this rearrangement is a concerted and asynchronous process in the gas phase. (C) 1999 Elsevier Science Ltd. All rights reserved.