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

Grigg R., Kongkathip N., Kongkathip B., Luangkamin S., DÖNDAŞ H. A.

TETRAHEDRON, vol.57, no.37, pp.7965-7978, 2001 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 57 Issue: 37
  • Publication Date: 2001
  • Doi Number: 10.1016/s0040-4020(01)00771-2
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7965-7978
  • Keywords: chromans, dihydrobenzofurans, atom economy, Claisen rearrangement, cyclisation, CARBON-MONOXIDE, REARRANGEMENT, COMPLEXES, ARYL, NUCLEOPHILES, ALDEHYDES, IODIDES
  • Çukurova University Affiliated: No

Abstract

A 3-step 100% atom economic sequence is reported whereby a variety of phenols react with 2 mol equiv. of allene to give phenoxymethyl-1,3-dienyl ethers. Subsequent thermal Claisen rearrangement to C-1,3-dienes and acid catalysed ring closure furnishes 3:1-6.5:1 mixtures of exo-methylene chromans and dihydrobenzofurans with the former predominating. (C) 2001 Elsevier Science Ltd. All rights reserved.