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 this procedure to several substituted phthalans (1b-i) was investigated, and the regiochemistry as well as the synthetic usefulness of these reactions are discussed
Electron-transfer-induced reductive cleavage of phthalans: Reactivity and synthetic applications / Azzena, Ugo Gavino; Salvatore, Demartis; Giovanni, Melloni. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 61:(1996), pp. 4913-4919. [10.1021/jo9604548]
Electron-transfer-induced reductive cleavage of phthalans: Reactivity and synthetic applications
AZZENA, Ugo Gavino;
1996-01-01
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 this procedure to several substituted phthalans (1b-i) was investigated, and the regiochemistry as well as the synthetic usefulness of these reactions are discussedI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
