REACTION OF 1-PHENYLCYCLOOCTENE WITH NBS. SYNTHESIS OF ALLYLIC ALCOHOLS AND 1,3-DIENES

Bülent Büyükkıdan,* İ. Gökay Budak, and Mustafa Ceylan

Department of Chemistry, Faculty of Science, Gaziosmanpasa University, 60240, Tokat, Turkey

Fax: +90-3562521585, E-mail: bbuyuk@gop.edu.tr

Abstract

Reaction of 1-phenylcyclooctene (3) with NBS resulted in the formation of a mixture of products (4-8). After column chromatography, we isolated the vinyl bromide 14 and 1,3‑dienes 9, 10, bromo-1, 3-dienes 11, 12 and allylic alcohol 15. Reaction of the mixture (4-8) with AgClO₄ afforded compounds 9, 14, 15 and a,b-unsaturated ketones 21 and 22.