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An efficient synthesis of dialkyl 2-(diphenoxyphosphoryl)-3-(alkylthio)succinates from alkylthiols, triphenyl phosphite and dialkyl acetylenedicarboxylates

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Abstract

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 3 J 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.

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Authors and Affiliations

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

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

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  1. I. Yavari
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  2. R. Hajinasiri
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  3. S. Z. Sayyed-Alangi
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  4. N. Iravani
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Correspondence to I. Yavari.

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Yavari, I., Hajinasiri, R., Sayyed-Alangi, S.Z. et al. An efficient synthesis of dialkyl 2-(diphenoxyphosphoryl)-3-(alkylthio)succinates from alkylthiols, triphenyl phosphite and dialkyl acetylenedicarboxylates. JICS 6, 705–709 (2009). https://doi.org/10.1007/BF03246159

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  • DOI: https://doi.org/10.1007/BF03246159

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