5032-98-4Relevant academic research and scientific papers
Microwave assisted intramolecular wittig reaction: A facile method for the synthesis of conjugated acetylenes
Rao, V. V. V. N. Rama,Ravikanth,Reddy, G. Venkat,Maitraie,Yadla,Rao, P. Shanthan
, p. 1523 - 1529 (2007/10/03)
A rapid and efficient synthesis of acetylenic compounds by the microwave assisted intramolecular Wittig reaction of β-oxo-alkylidene-triphenylphosphoranes is reported.
(Cyanomethylene)phosphoranes as Novel Carbonyl 1,1-Dipole Synthons: An Efficient Synthesis of α-Keto Acids, Esters, and Amides
Wasserman, Harry H.,Ho, Wen-Bin
, p. 4364 - 4366 (2007/10/02)
Carboxylic acids react with (cyanomethylene)triphenylphosphorane in the presence of EDCI to form cyano keto phosphoranes.The resulting ylides may then be oxidatively cleaved with ozone to form α,β-diketonitriles.These highly electrophilic products may then be converted in situ to α-keto acids, esters, and amides.
Reaction of Triphenylphosphine Radical Cation with 1,3-Dicarbonyl Compounds: Electrochemical One-Step Preparation of Dioxomethylenetriphenylphosphoranes
Ohmori, Hidenobu,Maeda, Hatsuo,Tamaoka, Mie,Masui, Masaichiro
, p. 613 - 620 (2007/10/02)
Electrochemical oxidation of Ph3P (1) in MeCN in the presence of 1,3-dicarbonyl compounds, R1COCH2COR2 (3), with HClO4 as the supporting electrolyte resulted in the formation of the phosphonium salts, Ph3P+ -CH(COR1)COR2 ClO4- (4), provided that R1 and/or R2 is a phenyl group.On the other hand, electrolysis in CH2Cl2 with 2,6-lutidinium perchlorate gave the phosphoranes, Ph3P=C(COR1)COR2 (5), directly from 1 and 3 in fair to excellent yields: in this case, R1 or R2 need not necessarily be a phenyl group.Thus, the electrolysis is shown to be a convenient method to prepare 5 in a single step.Plausible processes for the formation of 4 and 5 are proposed, involving the reaction of electrochemically generated Ph3P+. with the enol form of 3 as the keystep.Keywords - triphenylphosphine; 1,3-dicarbonyl compound; dioxomethyltriphenylphosphonium perchlorate; dioxomethylenetriphenylphosphorane; electrochemical oxidation; constant current electrolysis
Reaction of β-aminocinnamonitrile and its N-mono- and NN-di-substituted derivatives with benzonitrile oxides
Corsaro, Antonino,Chiacchio, Ugo,Purrello, Giovanni
, p. 2154 - 2157 (2007/10/05)
β-Aminocinnamonitrile (4a) reacts with benzonitrile oxides (2) to give, as primary products, the 3-aryl-5-(β-aminostyryl)-1,2,4-oxadiazoles (6) together with lesser amounts of 3-aryl-4-cyano-5-phenylisoxazoles (3). In the case of p-nitrobenzonitrile -xide (2c), 3-(p-nitrophenyl)-5-phenyl-1,2,4- oxadiazole (7) is also obtained. The N-monosubstituted aminocinnamonitriles behave similarly, whereas the NN-disubstituted compounds yield only the 3-aryl-4-cyano-5-phenylisoxazoles (3). A mechanism is proposed.
