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Addition of hypobromous acid to 1-phenylcycloalkenes
Authors:M Ceylan  E Findik  E Sahin  C Kazaz
Institution:1.Department of Chemistry, Faculty of Arts and Science,Gaziosmanpasa University,Tokat,Turkey;2.Department of Chemistry, Faculty of Arts and Science,Atatürk University,Erzurum,Turkey
Abstract: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-l-phenylcyclohexanol. The oxidation of allylic alcohols with pyridinium chlorochromate afforded the corresponding α,β-unsaturated ketones.
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