ChemInform Abstract: REACTION OF N‐DIETHOXYPHOSPHORYLTRIFLUOROACETIMIDOYL CHLORIDE WITH TRIETHYL PHOSPHITE

Abstract

Das Imidoylchlorid (I) reagiert mit Triethylphosphit (II) zu einem durch Vakuumdestillation trennbaren Gemisch der Verbindungen (IV) und (V).

Phosphorylation of α-Haloimines: P-C vs. P-N Bond Formation

“…In this case, bipolar ion of type A is stabilized by elimination of ethylene and protonation of the nitrogen atom [52]. In contrast, Ndiethoxyphosphoryl trifluoroacetimidoyl chloride, irrespective of the reagent-ratio, reacts with two moles of triethylphosphite to produce a mixture of tri-and diphosphorylated difluorovinylamides 152 and 153 respectively [53]. The initially formed imidoyl phosphonate 151 is more reactive than starting imidoyl chloride 149 because of the activating effect of the phosphoryl group and, for this reason, it reacts quickly with a second molecule of triethylphosphite to produce a mixture (1:1) of N-phosphorylation (152) and N-alkylation products 153 (Scheme 49).…”

N-Functionally substituted imines of polychlorinated (brominated) aldehydes and ketones

“…Thus bis(dialkoxyphosphoryl)trichlorovinylamines react with two equivalents of a dialkylamine to give dialkyl N-(1-dialkylamino-2,2-dichloroethylidene) phosphoramidates 49a,b. 102 It has been mentioned above that imines with a similar structure have also been prepared from trichloroacetamidines. 93 (2,2-Dichloro-1-cyanovinyl)benzenesulfonamide 50 reacts with amines, in the opinion of the researchers cited, 103…”

“…102 It has been mentioned above that imines with a similar structure have also been prepared from trichloroacetamidines. 93 (2,2-Dichloro-1-cyanovinyl)benzenesulfonamide 50 reacts with amines, in the opinion of the researchers cited, 103…”

“…Dialkyl N-(1-amino-2,2-dichloroethylidene) phosphoramidates were prepared by the reaction of trichloroacetylamidines with trialkyl phosphites. 93 Diethyl N-(1-dimethylamino-2,2,2-trichloroethylidene) phosphoramidate 31 was synthesised from N-chloro-N H ,N H -dimethyltrichloroacetylamidines and triethyl phosphite. 93 Trialkyl phosphites were shown 94 to react with polychloronitrosoethanes under mild conditions (7208C) giving rise to the corresponding dialkyl N-chloroalkylidene phosphoramidates 32a ± h.…”

Synthesis of Symmetrical N-Aryl-C-phosphonoacetamidines

“…17 Amidines bearing a phosphoryl group have been reported over several decades; 18,19 however, reports on the synthesis of symmetrical phosphonoamidines are rare. [20][21][22] Sinitsa and co-workers 20 reported the synthesis of N-alkylated symmetrical amidines by treating a (gem-dichlorovinyl)phosphonate with primary amines. An alternative preparation of symmetrical phosphonoamidines starting from a phosphorylated ketenimine had been reported by Motoyoshiya et al 22 Phosphonoketenimines and -ynamines, which are highly reactive species and useful synthetic intermediates, are suitable sources for obtaining phosphorylated amidines.…”