SYNTHESES OF 9-PHENYLSUFONYLIMINO-1,4-DIOXA-8,10-DIAZACYCLOTRIDECANES AND 9,22-BIS(PHENYLSULFONYLIMINO)-1,4,14,17-TETRAOXA-8,10,21,23-TETRAAZACYCLOHEXACOSANES - MACROCYCLIZATION VIA DIMETHYL N-PHENYLSULFONYLCARBONIMIDODITHIOATES

The reaction of dimethyl N-phenylsulfonylcarbonimidodithioates (1) with diamines gave three different types of products due to changes in the molar ratio of the starting materials. From aliphatic diamines heterocyclic 1 : 1 and acyclic 2: 1 reaction products were obtained. In order to prepare macrocycles, the reaction of 1 with 1,10-diamino-4,7-dioxadecane (10) was carried out. 1,1'-(4,7-Dioxadecamethylene)bis(2-methyl-3-phenylsulfonylisothiourea)s (11) and 9-phenylsulfonylimino-1,4-dioxa-8,10-diazacyclotridecanes were obtained by 2:1- and 1: 2-mixed reactions of 1 with 10, respectively. The 2:2 reaction products, 9,22-bis(phenylsulfonylimino)-1,4, 14,17-tetraoxa,8,10,21,23-tetraazacyclohexacosanes, were prepared from 1 and a greater excess of diamine 10 (1:4) or from 11 and diamine 10.