Abstract
The effect of the [2.2.2]cyclophane ring structure on the reduction of 1,2,5-thiadiazole ring incorporated in cyclophanes 1a-c and 2a-c was investigated. When reduced by sodium metal in ethanol followed by acetylation, para[2 3 ]cyclophane 1 gave a mixture of the expected cis- and trans-diamides, 3 and 4, in which 4 was the major product. On the other hand, reduction of 1 with lithium aluminum hydride proceeded in a cis-selective manner and gave 3 as a major product after a treatment of the reduced products with acetic anhydride. The reduction of metacyclophane 2, which is less strained than 1, proceeded exclusively in cis-fashion and a subsequent treatment of the reduction product with acetic anhydride gave only cis-diamide 6
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