Addition of hypobromous acid to 1-phenylcycloalkenes

Ceylan M., Findik E., ŞAHİN E., KAZAZ C.

RUSSIAN CHEMICAL BULLETIN, cilt.58, sa.11, ss.2299-2303, 2009 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 58 Sayı: 11
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1007/s11172-009-0321-y
  • Dergi Adı: RUSSIAN CHEMICAL BULLETIN
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2299-2303
  • Anahtar Kelimeler: 1-phenylcycloalkenes, allylic bromides, allylic alcohols, N-bromosuccinimide, alpha,beta-enones, BENZENE
  • Atatürk Üniversitesi Adresli: Evet

Özet

Reaction of 1-phenylcyclooctene and 1-phenylcycloheptene with N-bromosuccinimide (NBS) in aqueous DMSO gives the corresponding 3-bromo-2-phenylcycloalkenes and 2-phenylcycloalk-2-enols in a ratio of 3 : 1. Unlike them, 1-phenylcyclohexene gives a mixture of 3-bromo-2-phenylcyclohexene and 2-bromo-1-phenylcyclohexanol. The oxidation of allylic alcohols with pyridinium chlorochromate afforded the corresponding alpha,beta-unsaturated ketones.