Uncaging of Volatile Honey Bee Pheromones from Water-soluble Precursors

Abstract

The potential of using hydrazones as water-labile protecting groups on sulfonyl hydrazides has been explored. These sulfonyl hydrazides will eventually become water-soluble precursors of lipids and small hydrophobic molecules. Several hydrazinoacetates were synthesized by transesterification of commercial ethyl hydrazinoacetate. Ethyl and n-butyl hydrazinoacetate were then reacted with the photo protecting group NPPOC to form 'caged' molecules, followed by the reaction with a sulfonyl chloride such as para-nitrobenzenesulfonyl chloride to form the sulfonyl hydrazides. The synthesis of sulfonyl hydrazides was monitored by NMR spectroscopy, and then the products were irradiated with light to trigger the cleavage of the caging groups, releasing nitrogen and a sulfinate ion. The uncaging process was monitor by NMR spectroscopy, but the product mixtures were too complex to show the formation of the desired acetate esters.

Date of Award	1 Aug 2015
Original language	English
Awarding Institution	The University of Manchester
Supervisor	Simon Webb (Supervisor)