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

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

Volume: 11 Issue: 1

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

Affiliation:

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

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 ³J_PP 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.

Cite this article as:

Keglevich Gyorgy, Bálint Erika, Takács Judit, Drahos László, Huben Krzysztof and Jankowski Stefan, The Addition of Dialkyl Phosphites and Diphenylphosphine Oxide on the Triple Bond of Dimethyl Acetylenedicarboxylate under Solvent-Free and Microwave Conditions, Current Organic Synthesis 2014; 11 (1) . https://dx.doi.org/10.2174/1570179411999140304142747