City Research Online

Abstract

The mechanism and scope of the Pummerer reaction is reviewed.

Attempts to prepare the biogenetic precursors of resorcinols from dehydroacetic acid are described.

A convenient preparation of a y,é6-unsaturated aceto-acetate has been developed, and attempts to induce its aromatisation are discussed.

A novel one-step synthesis of 5-substituted resorcinols has been achieved by condensing methyl (phenylsulphiny1)-acetate (MPSA) with a,8-unsaturated methyl ketones. The isolation of the intermediate cyclohexanediones has been accomplished and their structures are discussed. In the case of olivetol, these compounds were converted to their enol ethers and the relative stereochemistries of the four products were deduced.

An analogous route to 3,5-disubstituted and 2,3,5-trisubstituted phenols is described. The scope of these reactions is investigated.
Some transformations of products derived from the alkylation of phenylsulphinylacetone (PSA) dianion are discussed. An unusual Pummerer rearrangement of MPSA and PSA has been observed.

A simple synthesis of an a,8-unsaturated, a-phenylsul-phinyl ester has been discovered. The potential of this type of compound as a synthetic intermediate is discussed and illustrated with examples.

Publication Type:	Thesis (Doctoral)
Subjects:	Q Science > Q Science (General) Q Science > QD Chemistry
Departments:	School of Science & Technology School of Science & Technology > School of Science & Technology Doctoral Theses Doctoral Theses

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