Tetrahedron Letters p. 2009 - 2012 (1998)
Update date:2022-08-16
Topics:
Altamura, Anna
D'Accolti, Lucia
Detomaso, Antonia
Dinoi, Anna
Fiorentino, Michele
Fusco, Caterina
Curci, Ruggero
Using dimethyldioxirane, the selective transfomation of aldehyde N,N-dimethylhydrazones into the corresponding nitrites was achieved in high yield and under mild conditions. The determination of the substituent effect on rates, along with an estimate of the primary kinetic isotope effect using PhCH=NNMe2 and PhCD=NNMe2 provided useful hints concerning the reaction mechanism. II was also observed that the nitrile products do not undergo further oxidation, even with excess dioxirane.
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