133610-24-9Relevant academic research and scientific papers
Reduction of the 1,2,5-Thiadiazole Ring of 3,6;12,15-Di-1,4-benzo(3,4)-1,2,5-thiadiazolo- and 3,5:11,13-Di-1,3-benzo(3,4)-1,2,5-thiadiazolocyclophanes: Selective Preparation of cis- and trans-3>Cyclophane-1,2-diacetoamide
Hatta, Taizo,Mataka, Shuntaro,Tashiro, Masashi,Numano, Katsutoshi,Suzuki, Hiroshi,Tori-i, Akiyoshi
, p. 55 - 59 (2007/10/02)
The effects of the 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, para3>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.
