The cycloaddition of cyclopropenes to enones

Authors
Al Dulayymi, JR Baird, MS Hussain, HH Alhourani, BJ Alhabashna, AMY Coles, SJ Hursthouse, MB
Citation
Jr. Al Dulayymi et al., The cycloaddition of cyclopropenes to enones, TETRAHEDR L, 41(21), 2000, pp. 4205-4208
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
21
Year of publication
2000
Pages
4205 - 4208
Database
ISI
SICI code
0040-4039(20000529)41:21<4205:TCOCTE>2.0.ZU;2-9
Abstract
A number of 1- and 1,2-disubstituted cyclopropenes undergo [4+2]-cycloaddit ion to methyl vinyl ketone or acrolein at ambient temperature to produce 2- oxabicyclo[4.1.0]hept-3-enes. When 1-phenyl-2-trimethylsilyl cyclopropene i s treated with 0.4 mel. equiv. of m-chloroperbenzoic acid, the derived ring -opened enone undergoes [4+2]-cycloaddition to the remaining starting mater ial at ambient temperature. (C) 2000 Elsevier Science Ltd. All rights reser ved.