The Journal of Organic Chemistry

syn-8, 16-Difluoro [2.2] metacyclophane-1, 9-diene

V Boekelheide, PH Anderson

Index: Boekelheide,V.; Anderson,P.H. Journal of Organic Chemistry, 1973 , vol. 38, p. 3928 - 3931

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Citation Number: 21

Abstract

cyclophane (5) by the condensation of 2, 6-bis (mercaptomethy1) toluene with 3. In this case 5 was formed with the ratio of syn to anti isomcrs being 3: 2. Similar results have been reported by Vogtle and n'e~ mann.~ Even in this instance the repulsion of a single fluoro group apparently outweighs the greater strain energy associated with the syn conformation. The important consequencc of the formation of only the syn conformer of 4 was that we'i\' ...