Preparation and some reactions of 3,5:8,10-di-1,3-benzo[8](3,4)-1,2,5-thiadiazolocyclophane

Abstract

Titled 1,2,5-thiadiazolometacyclophane 1 was prepared via thia[2.3]cyclophane 5 which was obtained by the reaction of di(bromomethyl) 2 with sodium sulfide under phase-transfer-catalysed conditions. Cyclophane 1 gave the corresponding pyrene derivatives by the oxidative transannular reaction in the reaction with brominating reagent. Reduction of 1 with lithium aluminium hybride followed by acetylation with acetic anhydride gave a 4:1-mixture of cis-and trans-diamide 11 and 12 with a trace amount of cyclophane-ring-cleaved product 13. On the other hand, 13 was obtained as a major product in the reduction with metal sodium and diisobutylaluminium hydride