The effect of substituents of alpha-alkyl sidechains on furan-diazoester interactions

Authors
Wenkert, E Khatuya, H
Citation
E. Wenkert et H. Khatuya, The effect of substituents of alpha-alkyl sidechains on furan-diazoester interactions, TETRAHEDR L, 40(30), 1999, pp. 5439-5442
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
30
Year of publication
1999
Pages
5439 - 5442
Database
ISI
SICI code
0040-4039(19990723)40:30<5439:TEOSOA>2.0.ZU;2-I
Abstract
Reactions of various alpha-alkyl-substituted furans with ethyl diazoacetate or methyl diazopropionate in the presence of Rh-2(OAc)(4), followed by iod ine-induced isomerization, yielded a variety of functionalized 1,3-diacyl-b utadienes (furan ring-unravelled products). Though with furfural and 2-acet ylfuran the reaction took place at the sidechain, with furfural acetal both the furan as well as acetal moities participated. (C) 1999 Elsevier Scienc e Ltd. All rights reserved.