Anchimeric assistance by the oxo group to the enoic function in 9-oxo-(E)-dec-2-enoic acid, the pheromone of the queen honeybee Apis mellifica: importance of the folded forms in solution

Abstract

Exchanges in D₂O with queen substance (1), the pheromone of the queen honeybee, the C₉ analogue (2), and (E)-dec-2-enoic acid (3), were determined by mass spectrometry and ¹H n.m.r. spectroscopy, the importance of the folded conformations through which the end functional groups interfere being emphasized for (1) and (2); this is the first demonstration of anchimeric assistance by an oxo group to a terminal enoic acid function in an aliphatic molecule.