Some studies on the ene reactions of allene sulphoxides

Abstract

One example of an allene sulphoxide behaving as an enophile in an intramolecular ene reaction to give a cyclopentene was known at the beginning of the project. A series of substrates was prepared to assess the generality of the reaction and an attempt to realise the potential of the reaction for natural product synthesis was made. Chapter Two describes attempts to form acyclic 1,4-dienes by the intermolecular ene reaction of 1-phenylsulphinyl-3-methylbuta-l,2-diene with a variety of alkenes under Lewis acid catalysis, or at high pressure or temperature. Some preliminary studies of the ene reactions of phenylsulphonylpropadiene are also described. Chapter Three concerns the extension of the intramolecular ene reaction to the preparation of six membered rings, the use of enols as ene components to give acylcyclopentenes and the preparation of a potential intermediate for the Iridoid sesquiterpenes. An attempt to prepare the insect defence pheromone, Chrysomelidial, by Pummerer rearrangement and hydrolysis of this intermediate is described. Chapter Four describes the use of the intramolecular ene reaction for the annelation of five membered rings and an attempt to take advantage of the functionality of the products obtained by this annelation to prepare medium ring compounds by means of a Grob fragmentation. An attempt to use the ene reaction for spiro-annelation, instead of giving the required spiro-[4,5]-decane gave a vinylsulphoxide containing the novel tricyclo [4,4,0,0^1,4] decane ring system.

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