69882-39-9Relevant academic research and scientific papers
Aromatic Phosphines with Second Order Substituents, XVI. - Phenylogous PO-activated Olefination: Synthesis of 4'-Donator Substituted 4-(Diphenylphosphinyl)stilbenes
Schiemenz, Guenter Paulus,Finzenhagen, Manfred
, p. 1476 - 1484 (2007/10/02)
Being a -M substituent, the 4-diphenylphosphinyl group acidifies the methyl group of toluene to a similar degree as a 4-cyano group.The carbanion formed by deprotonation reacts with N-benzylidene anilines to yield 4-(diphenylphosphinyl)stilbenes.In these, UV-spectroscopically the phosphorus on the one hand behaves like a -M substituent, on the other hand it acts as a barrier to through-conjugation.
Synthesis of trans-4-Diphenylphosphinyl Stilbenes
Gloyna, D.,Alder, L.,Henning, H.-G.,Koeppel, H.,Siegmund, M.,Schleinitz, K.-D.
, p. 237 - 246 (2007/10/02)
The reaction of 4-tolyl-diphenylphosphine oxide with N-bromosuccinimide results in 4-diphenylphosphinyl benzylbromide 5 which can be easily converted to (4-diphenylphosphinyl)-benzyl triphenylphosphonium bromide 6 and (4-diphenylphosphinyl)-benzyl diphenylphosphine oxide 7, respectively.In the presence of strong bases 6 and 7 react with aromatic aldehydes 8 to the 4-diphenylphosphinyl substituted stilbenes 1.The yields depend on the nature of base and solvent.The trans configuration of 1 is determined by i.r. and 1H-n.m.r. measurements.
