78564-51-9Relevant articles and documents
Photodecomposition of some para-substituted 2-pyrazolylphenyl azides. Substituents affect the phenylnitrene S-T gap more than the barrier to ring expansion
Albini, Angelo,Bettinetti, Gianfranco,Minoli, Giovanna
, p. 3104 - 3113 (2007/10/03)
A series of para-substituted (H, Me, Cl, F, CF3, OMe, NMe2) phenyl azides bearing a dimethylpyrazolyl group in position 2 allowing intramolecular trapping of singlet nitrene have been photolyzed at both 295 and 90 K in ethanol. For t
SYNTHESIS OF DIMETHYLPYRAZOLOBENZOTRIAZOLES AND OF METHYLPYRAZOLOQUINOXALINES BY CYCLIZATION OF 3,5-DIMETHYL-1-(2-NITRENOPHENYL)PYRAZOLES
Albini, Angelo,Bettinetti, Gianfranco,Minoli, Giovanna
, p. 597 - 606 (2007/10/02)
The thermal and photochemical decomposition of a series of 5-substituted 1-(2-azidophenyl)-3,5-dimethylpyrazoles has been examined under a homogeneous set of conditions.Cyclization to pyrazolobenzotriazole (via singlet nitrene) is an efficient process except when the phenyl substituent induces intersystem crossing to the azide triplet or compensates for its electrophilicity.On the contrary, cyclization to pyrazoloquinoxaline (via triplet nitrene) is not a preparatively useful process, due to competition with dimerization to the azo derivatives and reduction to aminophenylpyrazoles.
DIMETHYLBENZOPYRAZOLOTRIAZOLE vs METHYLPYRAZOLOQUINOXALINE FROM 3,5-DIMETHYL-1-(2-NITRENOPHENYL)PYRAZOLE
Albini, Angelo,Bettinetti, Gian Franco,Minoli, Giovanna
, p. 331 - 334 (2007/10/02)
The chemistry of singlet and triplet 3,5-dimethyl-1-(2-nitrenophenyl)pyrazole is examined.Intramolecular electron transfer is found to play a key role in determining the easy reaction to the ylide (VII) from the singlet state and the "lazyness" of the triplet state.