Stereoselective synthesis of highly functionalized cyclobutenes. A facile route to electron-deficient 1,3-dienes

Authors
Yavari, I Asghari, S
Citation
I. Yavari et S. Asghari, Stereoselective synthesis of highly functionalized cyclobutenes. A facile route to electron-deficient 1,3-dienes, TETRAHEDRON, 55(40), 1999, pp. 11853-11858
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
40
Year of publication
1999
Pages
11853 - 11858
Database
ISI
SICI code
0040-4020(19991001)55:40<11853:SSOHFC>2.0.ZU;2-S
Abstract
Acetoacetanilide undergoes a smooth reaction with triphenylphosphine and di alkyl acetylenedicarboxylates to produce dialkyl 2-(acetoacetanilide-2-yl)- 3-(triphenylphosphoranilidene)- butandioates, which undergo intramolecular Wittig reaction to produce 2-methyl-3-(N-phenylcarbonyl)-1,4-dialkoxycarbon ylcyclobutenes. These cyclobutene derivatives undergo electrocyclic ring-op ening reactions in boiling toluene to produce highly electron-deficient 1,3 -dienes. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.