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.
|Journal||Journal of the Chemical Society, Perkin Transactions 2|
|Publication status||Published - 1 Dec 1993|
Martin, X., Marquet, J., & Lluch, J. M. (1993). Carbon-oxygen alkyl ether fragmentation in the radical anions of phenyl and nitrophenyl methyl ethers. An AM1 study. Journal of the Chemical Society, Perkin Transactions 2, (1), 87-90.