Iron polyphthalocyanine reduction

Butyroin has been prepared by reductive condensation of ethyl butyrate with sodium in xylene, or with sodium in the presence of chloro-trimethylsilane. and by reduction of 4,5-octanedlone with sodium l-benzyl-3-carbamoyl-l,4-dihydropyridine-4-sulfinate in the presence of magnesium chloride or with thiophenol in the presence of iron polyphthalocyanine as electron transfer agent.This acyloin has also been obtained by oxidation of (E)-4-octene with potassium permanganate and by reaction of... 

A small number of papers that cover mechanistic aspects deal with the factors that stabilize the developing carbonium ion in the hydrolysis of 0,S-thioacetaIs. An electron-transfer, mild reduction system (iron polyphthalocyanine) has been shown to reduce benzil dithioacetal to the / -keto-sulphide [PhCOCPh(SPh)2 PhCOCHPhSPh]. Homolysis of dithioacetals on heating with BuKDOBu in PhCI followed by a 1,2-shift of an alkylthio-group leads to l,2-bis-(alkylthio)alkyl compounds/ ... 

The potent reductant Smh readily reduces a-alkylthio, a-sulfinyl and a-sulfonyl ketones at -78 °C A mixture of iron(II) polyphthalocyanine and thiophenol has been used to reduce a-halo, a-alkylthio, and a,a-bis(alkylthio) ketones. The iron compound apparently reacts as an electron transfer mediator the actual source of electrons is the thiophenol, which is converted to diphenyl disulfide in the course of the reaction. 

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