231289-36-4Relevant articles and documents
Synthesis of 1,3,4-thiadiazolines from 1,2-dithiole-3-thiones
Ogurtsov, Vladimir A.,Rakitin, Oleg A.,Rees, Charles W.,Smolentsev, Alexey A.
, p. 55 - 56 (2005)
The thiocarbonyl group of 4,5-dichloro-1,2-dithiole-3-thione reacts as a 1,3-dipolarophile towards diaryl nitrile imines by 1,3-dipolar cycloaddition followed by opening of the dithiole ring with loss of sulfur to give 5-methylene-1,3,4-thiadiazolines; th
Sydnone photochemistry: Direct observation of earl's bicyclic lactone valence isomers (oxadiazabicyclo[2.1.0] pentanones), formation of carbodiimides, reaction mechanism, and photochromism
Veedu, Rakesh N.,Kvaskoff, David,Wentrup, Curt
, p. 457 - 468 (2014/04/03)
The matrix photolyses of 3-phenyl-, 3-pyridyl, and 3,4-diphenylsydnones 16, 19, and 22 were investigated by matrixisolation infrared spectroscopy. The formation of the neutral, bicyclic lactone valence isomers postulated by Earl - the oxadiazabicyclo[2.1.0]pentanones exo-17 and exo-20 - was clearly observed in the first two cases and is also likely in the case of exo-23 (C=Oabsorptions in the IR at 1881, 1886, and 1874 cm -1, respectively). The efficient photodecomposition of sydnones to carbodiimides RN=C=NR0 (18, 21, and 24) and CO2 was established in all three cases. The formation of benzonitrile 27 and azacycloheptatetraene 29 in the matrix photolysis of diphenylsydnone 22 is indicative of diphenylnitrile imine PhCNNPh 26 as an intermediate (2340 cm -11). Neither bicyclic lactones nor carbodiimides have been observed previously in sydnone photochemistry. A general reaction mechanism for the formation of carbodiimides, nitrile imines, and photochromism is put forward. CSIRO 2014.
Regioselective 1,3-dipolar cycloaddition of nitrilimines to 2-methyl-2-vinyl oxirane
Yldrm, Muhammet,Dürüst, Yaar
experimental part, p. 3209 - 3215 (2011/05/30)
1,3-Dipolar cycloaddition of in situ generated C,N-diaryl nitrilimines to 2-methyl-2-vinyl oxirane gives rise to the regioselective formation of novel 5-(2-methyloxiranyl)-4,5-dihydropyrazole derivatives in moderate to good yields. The structures and ster