71556-62-2Relevant academic research and scientific papers
Reaction of Phosphinyl and Phosphinothioyl Disulfides with Diazomethane
Miyamoto, Toru,Yamamoto, Izuru
, p. 2581 - 2586 (2007/10/02)
Four kinds of 4-substituted phenyl diethoxyphosphinyl disulfide (substituents: H, CH3, C2H5, Cl) and phenyl diethoxyphosphinothioyl disulfide reacted readily with diazomethane.The phosphinyl disulfides produced diethyl (4-substituted phenylthio)methyl phosphorothionate and the isomer, diethyl S-(4-substituted phenylthio)methyl phosphorothiolate, as the main products, whereas the phosphinothioyl disulfide produced only diethyl S-(phenylthio)methyl phosphorodithioate.The possible mechanism involved is as follows: the S-S bond in (EtO)2P(X)-S-S-C6H4R (X=O or S) is cleaved by nucleophilic attack of diazomethane at the sulfur atom bonded to the phenyl group to produce and (+)N2CH2-S-C6H4R; the latter reacts with the former with loss of nitrogen; therefore, when X is O, two compounds, (EtO)2P(S)-O-CH2-S-C6H4R and (EtO)2P(O)-S-CH2-S-C6H4R, are produced, when X is S, only (EtO)2P(S)-S-CH2-S-C6H4R is obtained.
