An oxidative rearrangement of 6-phenylbicyclo[3.2.0]heptan-6-ol to 1,1'-biphenyl-carbaldehydes: A mechanistic study

Ceylan M., Findik E., SEÇEN H.

HELVETICA CHIMICA ACTA, cilt.91, sa.3, ss.559-568, 2008 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 91 Sayı: 3
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1002/hlca.200890058
  • Dergi Adı: HELVETICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.559-568
  • Atatürk Üniversitesi Adresli: Evet

Özet

Acid-catalyzed rearrangement of 6-phenylbicyclo[3.2.0]heptan-6-ol gave 1,1'-biphenyl and 1,1'-biphenyl-carbaldehydes in small amounts as well as the expected rearrangement products. A detailed study of the reaction mechanism revealed that the conversion occurs via an oxidative process through the consecutive formation of cycloheptadienes, cycloheptatrienes, and 1,1'-biphenyls. The acid-catalyzed rearrangement of 6-phenylbicyclo[3.2.0]hept-2-en-6-ols gave 1- and 2-phenylcycloheptatrienes directly, from which 1,1'-biphenyl and 1,1'-biphenyl-carbaldehydes were obtained by oxidation.