Photooxygenation of 5- and 6-chloro-1,3-cycloheptadienes and Reactions of their Endoperoxides with Base: Effects of the Chloro Substituent on the Reactions-Reference-Cited by-同舟云学术

Photooxygenation of 5- and 6-chloro-1,3-cycloheptadienes and Reactions of their Endoperoxides with Base: Effects of the Chloro Substituent on the Reactions

Published:2005-04 Issue:4 Volume:2005 Page:209-214
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Menzek Abdullah¹,Şengül M. Emin¹,Çetinkaya Yasin¹,Ceylan Selami¹

Affiliation:

1. Atatürk University, Faculty of Art and Sciences, Department of Chemistry, 25240 Erzurum, Turkey

Abstract

Photooxygenation reactions of 5- and 6-chlorocycloheptadienes 6 and 7 gave bicyclic endoperoxides 10–13. The endoperoxides 10 and 13 are major products due to the steric effects of the chloro substituent. The reactions of endoperoxide 10 with NEt3 under different conditions gave 1,4-epoxide 14, hydroxyenone 15, diketone 16, acetates 17–19 and diacetate 20. The reaction of endoperoxide 10 with pyridine and Ac2O gave diacetate 20 and dienone 21. The reaction of endoperoxide 13 with NEt3 gave tropone. The effects of the chloro substituent are discussed.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/0308234054213492

Reference21 articles.

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