125312-49-4Relevant academic research and scientific papers
The substituent effect of the phosphaalkenyl group
Termaten, Arjan,Van der Sluis, Marcel,Bickelhaupt, Friedrich
, p. 2049 - 2055 (2003)
Several novel phosphaalkenes (E)-Mes*P=CHC6H4X (6; X = Me3Si, Me3Sn, CHO, COOH, CN) were prepared and, together with other known members of this series, subjected to an analysis of linear free-energy relationships based on the values of pKa and values of δ(13Cpara) of substituted benzoic acids and on the values of δ(13Cpara) of substituted bromobenzenes. These analyses indicate that the (E)-es*P=CH group is a weak electron donor with a predominantly inductive effect (δp = -0.1) on a neighboring benzene ring; resonance interactions are of minor importance. This result shows that the P=C bond is surprisingly analogous to the C=C bond, and thus confirms the well-known diagonal relationship in the Periodic System between carbon and phosphorus atoms. The relationship between X and the values of δ(31P) of 6 is quite pronounced. It confirms the dominance of inductive interactions on the value of δ(31P); only with strongly electron-donating substituents may a certain degree of resonance interaction be involved. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Reductive coupling of two aldehydes to unsymmetrical: E -alkenes via phosphaalkene and phosphinate intermediates
Mai, Juri,Arkhypchuk, Anna I.,Gupta, Arvind Kumar,Ott, Sascha
, p. 7163 - 7166 (2018/07/03)
Stilbenes with push-pull electronics are directly accessible from an electron-rich and an electron-deficient benzaldehyde in a novel reductive aldehyde cross-coupling reaction. The one-pot procedure is enabled by the oxidation of a transient phosphinite to the corresponding phosphinate which exhibits sufficient reactivity towards deactivated aldehydes.
