Chemistry of hop constituents. Part XXXI. Spectroscopic determination of the fine structures of imines derived from lupones and agglomerone

Abstract

The fine structure of agglomerone is discussed and the major tautomer identified as (I). Agglomerone “imine” is concluded to be an enamine, with the amino-group in the side-chain, as (IV). Lupone and its congeners similarly yield crystalline products with ammonia but these have different spectroscopic characteristics (u.v., i.r., and ¹H n.m.r.) pointing to acylcyclohexane-imine structures (X).