
%0 Journal Article
%A Lap, BV 
%A Williams, LR 
%T Stereospecific reactions of <I>cis</I>- and <I>trans</I>-3-Aminochroman-4-ols
%J Australian Journal of Chemistry
%D 1977/10/01
%V 30
%N 10
%P 2205-2211
%K 
%R https://doi.org/10.1071/CH9772205
%U https://www.publish.csiro.au/paper/CH9772205 
%X Stereospecific reactions of epimeric 3-amino-6-methylchroman-4-ols (1 and 2; R = Me) have provided chemical evidence for their configuration and have led us to reverse the configurations that we had assigned previously to the 6-bromo analogues on the basis of N.M.R. data.     The 2-chloro-N-(4-hydroxy-6-methylchroman-3-yl)acetamides (3) and (4) were treated with potassium hydroxide in ethanol in an attempt to effect ring closure. The cis-chloroacetamide (4) gave a cyclic amide (5) while the trans-chloroacetamide (3) reacted with solvent to form the trans-3-ethoxyacetamidochroman-4-ol (6).     The configurations of the amino alcohols were confirmed by a study of their reactions with nitrous acid where deamination of the cis-amino alcohol gave the chroman-4-one (9) while the trans-amino alcohol gave a trans-diol (10) by an epoxide intermediate. 
