Unique zeolite-catalyzed synthesis of nitroketene S,N-acetals

Article abstract of DOI:10.1016/S0040-4020(01)86309-2

Dimethyl carbonimidodithioates (4a-g, 7a-c) derived from various primary amines and amino acid esters [glycine, (L)-alanine and (L)-phenylalanine] have been condensed with nitromethane in the presence of the rare-earth exchanged zeolite RE(70%)Na Y to give the S,N-acetals (5a-g, 8a-c). Mercuric chloride catalyzed hydrolysis of these (8a-c) has led to the nitroacetyl derivatives (9a-c). The glycine derivative (7a) gives a dimeric product (11) when heated alone with the zeolite.