1, 2-Cycloadditions to cis-5, 6-dichlorohexafluorocyclohexa-1, 3-diene

WP Dailey, P Ralli, D Wasserman…

Index: Dailey; Ralli; Wasserman; Lemal Journal of Organic Chemistry, 1989 , vol. 54, # 23 p. 5516 - 5522

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Citation Number: 21

Abstract

Addition of difluorocarbene to the title compound (7) at temperatures of 160-190" C yielded rearranged monoadducts having the norbornene and bicyclo [3.2. 0] hept-2-ene skeletons. Dechlorination of these compounds gave octafluoronorbornadiene (21) and octafluorobicyclo [3.2. 0] hepta-2, 6-diene (22). Though attempts to transform 22 into tropylium ion 1 met with failure, norbornadiene 21 was so transformed, as elaborated ...