Metal-catalyzed ylide formation and [2,3] sigmatropic rearrangement of allyl sulfides with trimethylsilyldiazomethane

Authors
Carter, DS Van Vranken, DL
Citation
Ds. Carter et Dl. Van Vranken, Metal-catalyzed ylide formation and [2,3] sigmatropic rearrangement of allyl sulfides with trimethylsilyldiazomethane, TETRAHEDR L, 40(9), 1999, pp. 1617-1620
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
9
Year of publication
1999
Pages
1617 - 1620
Database
ISI
SICI code
0040-4039(19990226)40:9<1617:MYFA[S>2.0.ZU;2-M
Abstract
Trimethylsilyldiazomethane is compared with ethyl diazoacetate for the rhod ium, copper, and cobalt catalyzed formation and [2,3] rearrangement of ally lsulfonium ylides. At room temperature, the reaction can be carried out usi ng the allyl sulfide as the limiting reagent by slow addition of 3 equivale nts of the diazo compound. Slightly better yields were obtained with trimet hylsilyldiazomethane than with ethyl diazoacetate. (C) 1999 Elsevier Scienc e Ltd. All rights reserved.