An oxidative rearrangement of 6-phenylbicyclo[3.2.0]heptan-6-ol to 1,1'-biphenyl-carbaldehydes: A mechanistic study
HELVETICA CHIMICA ACTA, cilt.91, sa.3, ss.559-568, 2008 (SCI-Expanded, Scopus)
- 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.