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An Efficient Synthesis of Dialkyl 2-(Diphenoxyphosphoryl)-3-(alkylthio)succinates from Alkylthiols, Triphenyl Phosphite and Dialkyl  Acetylenedicarboxylates

I. Yavari*, R. Hajinasiri, S.Z. Sayyed-Alangi and N. Iravani

Chemistry Department, Science and Research Branch, Islamic Azad University, Tehran, Iran

An efficient synthesis of dialkyl 2-(diphenoxyphosphoryl)-3-(alkylthio)succinates, as a mixture of two diastereomers, in 78-90% yields, is described via reaction between alkylthiols, dialkyl acetylenedicarboxylates, and triphenyl phosphite. The structures of products were deduced from their high-field ¹H, ¹³C, and ³¹P NMR spectra, and IR spectral data. Since these hosphonate esters possess two stereogenic centers, two diastereomers with gauche HCCH arrangements are possible. Observation of ³J_HH = 3.5-4.6 Hz for the vicinal methine protons confirmed the dominance of the gauche arrangement. A mechanism is proposed for the formation of products.

Keywords: Alkylthiols, Triphenyl phosphite, Acetylenic esters, Alkylthiosuccinates, Alkylphosphonates