REACTIONS OF 2,2-DIMETHYL-3-PHENYLAZIRINE WITH HYDRAZINO AND AMINO ALCOHOLS

Article abstract of DOI:10.1007/BF00503532

The reaction of 2,2-dimethyl-3-phenylazirine with β-hydrazino alcohols leads to the corresponding β-hydroxyalkylhydrazones of 2-amino-2-methyl-1-phenyl-1-propanone.The reaction of the same azirine with β- ang γ-amino alcohols gives primarily substituted oxazolidines and perhydro-1,3-oxazine, respectively, which undergo isomerization to the chain form, viz., the corresponding N-(2-amino-2-methyl-1-phenylpropylidene)amino alcohols; the tendency to undergo isomerization to the chain form is not manifested in the case of β-aminoethanol.A conclusion regarding the preferred conformation of the oxazolidines was drawn on the basis of the data from 1H and 13C NMR spectroscopy.The product of the reaction of azirine with α-aminoethanol is 2,5,5-trimethyl-4-phenyl-3-imidazoline.