Carbon-oxygen alkyl ether fragmentation in the radical anions of phenyl and nitrophenyl methyl ethers. An AM1 study

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Abstract

Alkyl ether fragmentations of radical anions of several phenyl and nitrophenyl methyl ethers have been theoretically studied by means of the AM1 semiempirical method. The cleavage occurs through a π*-σ* intramolecular electron transfer process, that is made possible by the lengthening of the C-O alkyl ether bond. The C-O scission is slowed down by the introduction of substituents that increase the σ*-π* energy gap.
Original languageEnglish
Pages (from-to)87-90
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number1
Publication statusPublished - 1 Dec 1993

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