Synthesis of N,P,S,Se-containing mono- and bicyclic compounds in reactions of isothiocyanato- and diisothiocyanato(di)chloromethyl(thio) phosphonates with hydrosulfur(seleno) compounds
✍ Scribed by R. M. Kamalov; G. S. Stepanov; L. F. Chertanova; A. A. Gazikasheva; M. A. Pudovik; A. N. Pudovik
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 949 KB
- Volume
- 3
- Category
- Article
- ISSN
- 1042-7163
No coin nor oath required. For personal study only.
✦ Synopsis
Reactions o f phenyl isothiocyanato (di) chloromethyl(thio)phosphonates (1) with thiols in the presence of a base give rise to 2-alkylthio-4,5-dihydro-4oxo(th ioxo)-4-phenoxy-I ,3,4-th iazaphospholes (5). Some of these compounds can also be obtained by alkylation o f 2,4-dithioxo-4-phenoxy-l,3,4-thiazaphospholidine (4), which is formed in the reaction of phenyl isothiocyanatochloromethylthiophosphonate (la) with sodium hydrosulfide. The interaction of la with HzSe und triethylamine results in the formation of 2,4-dithioxo-4-phenoxy-l,3,4-~elenazaphospholidine (8), which when alkylated affords 2-alkylthio-4,5-
dihydro-4-phenoxy-4-thioxo-l,3,4-~elenazaphospholes ( 9 ) Diisothiocyanatodichloromethyl(thio)-
phosphonates (1 1) react with a-toluenethiol in the presence of a base, giving rise to 3,7bis(benzy1thio)-I -oxo(thiono)bicyclo[3.3.U]-4,6-dithia-2,8-diaza-l-phosphaocta-2, 7-dienes ( 13). By the interaction of phenyl isothiocyanatotrichloromethylthiophosphonate (14) with ethanethiol and Et,N, S-ethyl-N-( 0-phenyI( trichloromethy1)thiophosphonyl)dithiocarbamate triethylarnmonium salt (15) has been formed. The molecular structures of some