79749-94-3Relevant academic research and scientific papers
EXTENDED ENOLATE IONS FROM γ-PHENYLTHIO-CROTONATE ESTERS
Brownbridge, Peter,Hunt, Paul G.,Warren, Stuart
, p. 3391 - 3394 (2007/10/02)
Substituted γ-phenylthio-crotonate esters (7) can be made by and PhS shifts: they form extended enolate anions which react with electrophiles at the carbon atom α to the carbonyl group and γ to sulphur.
Synthesis of Butenolides from α-(Phenylthio)-ketones and -esters: Crystal Structure of an Intermediate β-Phenylthio-γ-lactone
Brownbridge, Peter,Egert, Ernst,Hunt, Paul G.,Kennard, Olga,Warren, Stuart
, p. 2751 - 2759 (2007/10/02)
Alkylation of α-(phenylthio)-ketones or -esters with iodoacetate anion gives 1,4-dicarbonyl compounds which are reduced stereoselectively to β-phenylthio-γ-butyrolactones.Oxidation to sulphoxides and thermolysis provides a general synthesis of β- and γ-substituted Δαβ-butenolides.Treatment of 5,5-dimethyl-4-oxo-3-(phenylthio)-hexanoic acid with NaBH4 gives a single γ-lactone whose PhS and But groups are shown to be cis by X-ray crystal structure determination.
