
%0 Journal Article
%A Bapat, JB 
%A Black, DS 
%T Nitrones and oxazirans. I. Preparation of 1 -pyrroline 1-oxides and 1-pyrrolines by reductive cyclization of &#947;-nitro carbonyl compounds
%J Australian Journal of Chemistry
%D 1968/10/01
%V 21
%N 10
%P 2483-2495
%K 
%R https://doi.org/10.1071/CH9682483
%U https://www.publish.csiro.au/paper/CH9682483 
%X A series of new pyrroline I-oxides and their related pyrrolines is described. Preparation of these compounds by reductive cyclization of y-nitro carbonyl compounds is discussed. This method is critically dependent on the reducing agent in the preparation of pyrroline 1-oxides and various procedures are assessed. Zinc in aqueous ammonium chloride is successful only in the formation of 2-aryl-5,5-dimethyl-substituted pyrroline 1-oxides and reduced iron in a mildly acidic medium is the method of choice for the corresponding 2-alkyl-substituted compounds. Pyrrolines were prepared either by deoxygenation of pyrroline 1-oxides or reductive cyclization of suitable &#947;-nitro carbonyl derivatives. Details of the N.M.R. spectra of these compounds are discussed. 
