Sequential rearrangement reactions of benzhomonorbornadiene derivatives: Synthesis of 7-vinylbenzonorbornadiene

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Menzek A., Gökmen M.

Helvetica Chimica Acta, vol.86, no.2, pp.324-329, 2003 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 86 Issue: 2
• Publication Date: 2003
• Doi Number: 10.1002/hlca.200390034
• Journal Name: Helvetica Chimica Acta
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.324-329
• Uşak University Affiliated: No

Abstract

The reaction of alcohol 12 with SOCl2 gave chlorides 13 and 14, and the acetolysis of toluene-4-sulfonate 15 gave sequential rearrangement products 16, 17, and 18. In the reaction of 12, 13 is the major product of sequential rearrangements. Treatment of chloride 13 with t-BuOK gave 7-vinylbenzonorbornadiene 19.