106689-97-8Relevant academic research and scientific papers
ADDITION D'AROYL-2 AZIRIDINES, YLURES D'AZOMETHINE POTENTIELS, AUX ISOCYANATE ET ISOTHIOCYANATE DE PHENYLE.
Benhaoua, Hadj,Texier, Fernand,Toupet, Loic,Carrie, Robert
, p. 1117 - 1126 (2007/10/02)
The cycloaddition of azomethine ylids, generated from the thermal ring opening of aroylaziridines, occurs at the CN double bond of phenylisocyanate in accordance with previous work in the area.The literature claimed a different behaviour with phenylisothiocyanate.We have shown that the author's assumptions are based on incorrect structure determination of the products.The addition occurs also on the CN double bond of phenylisothiocyanate and the evolution of the primary adduct (i.e. a thioimidazolidone) is explained by the formation of a biradical stabilized through a capto-dative effect.This biradical cyclises to the transient 1,3 thiazolidine 12A.
ADDITION DE CYANO-2 AZIRIDINES, YLURES D'AZOMETHINE POTENTIELS AUX ISOCYANATES
Benhaoua, Hadj,Texier, Fernand,Carrie, R.
, p. 2283 - 2292 (2007/10/02)
The addition of azomethine ylids resulting from the thermal ring opening of the corresponding 2-cyanoaziridines on methyl and phenyl isocyanates occured exclusively at the C=N double bond.Only one orientation of the addition was observed and a mixture of diastereoisomeric imidazolidones was obtained in each case.On the basis of X ray structure of one diastereoisomer the stereochemistry of the other imidazolidones was established by NMR considering the long range coupling constants values between H2 and H5 (Jcis trans).The reaction of sodium methylate with the imidazolones led to imidates resulting from a nucleophilic addition on the nitrile function on the C2 carbon atom of the heterocycles.These imidates are easily hydrolyzed to the corresponding esters.If the reaction was carried out in the presence of oxygen the CHCN group was transformed into C=O group via the oxidation of the C2 carbanion.
