Palladium catalysed reaction of allene with phenols. Phenoxymethyl-1,3-dienes and their further reactions

Authors
Grigg, R Kongkathip, N Kongkathip, B Luangkamin, S Dondas, HA
Citation
R. Grigg et al., Palladium catalysed reaction of allene with phenols. Phenoxymethyl-1,3-dienes and their further reactions, TETRAHEDRON, 57(37), 2001, pp. 7965-7978
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
37
Year of publication
2001
Pages
7965 - 7978
Database
ISI
SICI code
0040-4020(20010910)57:37<7965:PCROAW>2.0.ZU;2-D
Abstract
A 3-step 100% atom economic sequence is reported whereby a variety of pheno ls react with 2 mol equiv. of allene to give phenoxymethyl-1,3-dienyl ether s. Subsequent thermal Claisen rearrangement to C-1,3-dienes and acid cataly sed ring closure furnishes 3:1-6.5:1 mixtures of exo-methylene chromans and dihydrobenzofurans with the former predominating. (C) 2001 Elsevier Scienc e Ltd. All rights reserved.