An efficient synthesis of dialkyl 2-(diphenoxyphosphoryl)-3-(alkylthio)succinates from alkylthiols, triphenyl phosphite and dialkyl acetylenedicarboxylates |
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Authors: | I Yavari R Hajinasiri S Z Sayyed-Alangi N Iravani |
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Institution: | 1. Chemistry Department, Science and Research Branch, Islamic Azad University, Tehran, Iran
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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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