Darzens glycidic ester synthesis

An illustrative example of oxirane formation by the action of alkali on a / -halohydrin is to be found in the reaction sequence involved in the Darzens glycidic ester synthesis (Section 5.7.6, p. 598). Three target molecules, namely 2-phenylaziridine (4), methyl (S)-thiiranecarboxylate (5) and cyclooctene sulphide (6), are selected here to exemplify this intramolecular cyclisation reaction type. 

Gerlach and Wetter (11) achieved rather better levels of control, also using catalytic hydrogenation for the relative stereochemistry between C-3 and C-6 (Scheme 3). 2-Furylacetone 25 was prepared by a Darzens glycidic ester synthesis from furfural, and was functionalised at the 5-position using Eschenmoser s 2-chloro-Af-cyclohexyl-propionaldonitrone 26 in the presence of... 

Several reactions formally involve enolates. but the course of the reaction is altered by the presence of reactive functionality. The Darzens glycidic ester synthesis discussed in Section 9.4.B.vi is one example. 

C. Epoxy Compounds via the Darzens Glycidic Ester Synthesis. 100... 

Benzilic acid rearrangement Benzoin reaction (condensation) Blanc chloromethylation reaction Bouveault-Blanc reduction Bucherer hydantoin synthesis Bucherer reaction Cannizzaro reaction Claisen aldoi condensation Claisen condensation Claisen-Schmidt reaction. Clemmensen reduction Darzens glycidic ester condensation Diazoamino-aminoazo rearrangement Dieckmann reaction Diels-Alder reaction Doebner reaction Erlenmeyer azlactone synthesis Fischer indole synthesis Fischer-Speior esterification Friedel-Crafts reaction... 

Rosen, T. Darzens Glycidic Ester Condensation In Comprehensive Organic Synthesis Trost, B. M. Fleming, I., Eds. Pergamon Oxford, 1991, vol. 2, pp 409-439. (Review). 

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