A novel three-component reaction of triphenylphosphine, DMAD, and electron-deficient styrenes: facile synthesis of cyclopentenyl phosphoranes was written by Nair, Vijay;Deepthi, Ani;Beneesh, P. B.;Eringathodi, Suresh. And the article was included in Synthesis in 2006.Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:
The zwitterion formed from triphenylphosphine and DMAD (di-Me acetylenedicarboxylate) adds to electron-deficient styrenes to form stable cyclopentenyl phosphoranes in 23% to 80% yield. This is the first example of such a zwitterion in which the phosphine is incorporated into the addition product. A mechanism for the reaction is proposed. The mol. structure of the formed cyclopentenyl phosphorane (I) was determined by x-ray crystallog. This cyclopentenyl phosphorane did not undergo Wittig reaction with 4-nitrobenzaldehyde. The cyclopentenyl phosphoranes thus formed can be oxidized to cyclopentene 1,2-diones. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile).
2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts