Synthesis of tetraphenylphosphonium (thio)phosphorylthiobenzamides and hydrolytic degradation to Ph3P=O, H2S and phosphoryl(thio)benzamides: A route for crystal design of PhC(X)NHP(O)(OiPr)2 (X=S, O)

Abstract

Reactions of the sodium salts of PhC(S)NHP(Y)(OiPr) 2 (Y=S, HL I; O, HL II) with PPh 4Br in 96% aqueous EtOH leads to the corresponding compounds PPh 4L I,II. The structures of these compounds were investigated by IR, 1H, 31P{ 1H} NMR spectroscopies; their compositions were examined by microanalysis. Recrystallization of PPh 4L I,II from EtOH/H 2O solution (1:1, v/v) leads to the formation of HL II and PhC(O)NHP(O)(OiPr) 2 (HL III), respectively. The crystal structures of HL II,III are reported and compared with the previously reported polymorphs. © 2012 Elsevier B.V. All rights reserved.