542-13-2Relevant academic research and scientific papers
EFFECT OF THE NATURE OF THE LEAVING GROUP IN REACTIONS OF 2-X-N-ETHYLPYRIDINIUM SALTS WITH AMINES IN ACETONITRILE
Titskii, G. D.,Mitchenko, E. S.
, p. 1949 - 1954 (2007/10/02)
The rate-determining stage in the nucleophilic substitution reactions of 2-X-N-ethylpyridinium salts with piperidine in acetonitrile changes, depending on the nature of the leaving group X.In the case where X = Hlg the controlling stage is the formation of the C-N bond.When X = 4-NO2C6H4O3, 3,4-(NO2)2C6H3O, and 2,6-(NO2)2C6H3O, nucleophilic substitution at the carbon atom is controlled by cleavage of the C-X bond.Nucleophilic substitution at a carbon atom of the benzene ring predominates in the reaction of 2-(2,4-dinitrophenoxy)-N-ethylpyridinium salt with piperidine.
Reactions of Primary and Secondary Amines with Fluoronitrene Generated from Isopropyl N,N-Difluorocarbamate
Klopotek, David L.,Hobrock, Brice G.,Kovacic, Peter,Jones, Martin B.
, p. 1665 - 1667 (2007/10/02)
Isopropyl N,N-difluorocarbamate deaminates primary amines, RNH2, affording RH, N2, RNHCO2-i-C3H7, and RNH2*HF.With secondary amines, dibenzylamine gives bibenzyl, whereas pyrrolidine yields a ring-expansion product, 2,3,4,5-tetrahydropyridazine.The reactions are consistent with the generation of fluoronitrene and subsequent production of the intermediates RN=NH from RNH2 and R2N=N from R2NH.The advantages of using isopropyl N,N-difluorocarbamate as a source of fluoronitrene are discussed.
