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1 2007

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Synthesis of O-Arylxanthates Esters and Derivatives

Humeres E., Debacher N., de Souza E.

Polish Journal of Chemistry

2007

Vol. 81, nr 5-6

1071-1079

No successful attempts have been made to synthesize O-arylxanthate esters from metal salts with alkylating agents because the metal derivatives are too unstable for the effective synthesis of the esters. In this work, substituted R-phenylxanthates (R = H, p-MeO, o-Me, p-F) were obtained as barium salts that upon reaction with alkyl halides produced O-arylxanthate esters. The ethylaminolysis of methyl O-phenylxanthate formed diethyl thiourea as the final product because of the similar nucleofugality of phenoxy and ethylthioxy moieties. A new method was used to obtain N-ethyl O-p-methoxyphenylthioncarbamate from the reaction of p-methoxyphenol and N-ethylisothiocyanate in a heterogeneous mixture of dichloromethane and aqueous phosphate buffer, pH 7.