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, cilt.57, sa.37, ss.7965-7978, 2001 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 57 Sayı: 37
  • Basım Tarihi: 2001
  • Doi Numarası: 10.1016/s0040-4020(01)00771-2
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.7965-7978
  • Anahtar Kelimeler: chromans, dihydrobenzofurans, atom economy, Claisen rearrangement, cyclisation, CARBON-MONOXIDE, REARRANGEMENT, COMPLEXES, ARYL, NUCLEOPHILES, ALDEHYDES, IODIDES
  • Çukurova Üniversitesi Adresli: Hayır

Özet

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.