Electron-transfer-induced reductive cleavage of phthalans: reactivity and synthetic applications

U Azzena, S Demartis, G Melloni

Index: Azzena, Ugo; Demartis, Salvatore; Melloni, Giovanni Journal of Organic Chemistry, 1996 , vol. 61, # 15 p. 4913 - 4919

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Citation Number: 48

Abstract

The behavior of phthalan (1a) was investigated under conditions of electron transfer from alkali metals in aprotic solvents. Reaction with lithium in the presence of a catalytic amount of naphthalene in THF led to the reductive cleavage of an arylmethyl carbon-oxygen bond, with formation of a stable dilithium compound. Trapping of this intermediate with several electrophiles (alkyl halides, carbonyl derivatives, CO2) was successful. The extension of ...

~69%

~56%

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