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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

The Addition of Dialkyl Phosphites and Diphenylphosphine Oxide on the Triple Bond of Dimethyl Acetylenedicarboxylate under Solvent-Free and Microwave Conditions

Author(s): Gyorgy Keglevich, Erika Bálint, Judit Takács, László Drahos, Krzysztof Huben and Stefan Jankowski

Volume 11 , Issue 1 , 2014

Page: [161 - 166] Pages: 6

DOI: 10.2174/1570179411999140304142747

Price: $65

Abstract

The addition of dialkyl phosphites or diphenylphosphine oxide to the triple bond of dialkyl acetylenedicarboxylate may result in mono- and/or bisadducts. The ratio of the products may be influenced by the molar ratio of the reactants and the conditions (temperature of microwave irradiation and reaction time). Stereospecific 3JPP couplings were utilized in the assignments to the meso and racemic forms of the bisadducts. The bis(dialkylphosphonyl)-succinates were formed as a mixture of the corresponding meso form and racemate, while bis(diphenylphosphinoyl)-succinate was obtained as a racemate. The 31P–12CH–13CH–31P spin system of bis(dialkylphosphonyl)-succinates was subjected to a detailed NMR analysis supported by simulation.

Keywords: Dialkyl acetylenedicarboxylate, dialkyl phosphite, diphenylphosphine oxide, addition, microwave.


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