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
| Autor: | A. A. Gazikasheva, A. N. Pudovik, R. M. Kamalov, L. F. Chertanova, M. A. Pudovik, G. S. Stepanov |
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| Rok vydání: | 1992 |
| Předmět: | |
| Zdroj: | Heteroatom Chemistry. 3:115-125 |
| ISSN: | 1098-1071 1042-7163 |
| DOI: | 10.1002/hc.520030206 |
| Popis: | Reactions of phenyl isothiocyanato(di)chloro-methyl(thio)phosphonates (1) with thiols in the presence of a base give rise to 2-alkylthio-4,5-dihydro-4-oxo(thioxo)-4-phenoxy-1,3,4-thiazaphospholes (5). Some of these compounds can also be obtained by alkylation of 2,4-dithioxo-4-phenoxy-1,3,4-thiazaphospholidine (4), which is formed in the reaction of phenyl isothiocyanatochloromethylthiophosphonate (1a) with sodium hydrosulfide. The interaction of 1a with H2Se and triethylamine results in the formation of 2,4-dithioxo-4-phenoxy-1,3,4-selenazaphospholidine (8), which when alkylated affords 2-alkylthio-4,5-dihydro-4-phenoxy-4-thioxo-1,3,4-selenazaphospholes (9) Diisothiocyanatodichloromethyl(thio)-phosphonates (11) react with α-toluenethiol in the presence of a base, giving rise to 3,7-bis(benzylthio)-1-oxo(thioxo)bicyclo[3.3.0]-4,6-dithia-2,8-diaza-1-phosphocta-2, 7-dienes (13). By the interaction of phenyl isothiocyanatotrichlorome-thylthiophosphonate (14) with ethanethiol and Et3N, S-ethyl-N-(O-phenyl(trichloromethyl)thiophosphonyl)dithiocarbamate triethylammonium salt (15) has been formed. The molecular structures of some P,N,S,Se-containing heterocycles that we have synthesized have been studied by X-ray diffraction. |
| Databáze: | OpenAIRE |
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