Facile dibromoolefination of lactones using bromomethylenetriphenylphosphorane

Authors
Lakhrissi, Y Taillefumier, C Chretien, F Chapleur, Y
Citation
Y. Lakhrissi et al., Facile dibromoolefination of lactones using bromomethylenetriphenylphosphorane, TETRAHEDR L, 42(41), 2001, pp. 7265-7268
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
41
Year of publication
2001
Pages
7265 - 7268
Database
ISI
SICI code
0040-4039(20011008)42:41<7265:FDOLUB>2.0.ZU;2-O
Abstract
Dibromoolefination of lactones was achieved in high yields using bromomethy lenetriphenylphosphorane in refluxing tetrahydrofuran. This reaction is bel ieved to proceed via bromination of the monobromophosphorane from the corre sponding bromomethyltriphenylphosphonium bromide with concomitant formation of methylenetriphenylphosphorane as shown by P-31 NMR. Transylidation shou ld Occur to afford the reactive dibromomethylenetriphenylphosphorane. (C) 2 001 Elsevier Science Ltd. All rights reserved.