Electron Apportionment in Cleavage of Radical Anions. 2. Naphthylmethyl Phenyl Ethers vs. Naphthyl Benzyl Ethers

Przemyslaw Maslak; Robert D. Guthrie

doi:10.1021/ja00270a022

Electron Apportionment in Cleavage of Radical Anions. 2. Naphthylmethyl Phenyl Ethers vs. Naphthyl Benzyl Ethers

Przemyslaw Maslak, Robert D. Guthrie

Chemistry

Research output: Contribution to journal › Article › peer-review

48 Scopus citations

Abstract

Naphthylmethyl phenyl ethers and naphthyl benzyl ethers were found to undergo scission of the H₂C-O bond when treated with radical anions of anthracene or fluoranthene. Under comparable conditions, ethers of the naphthylmethyl phenyl series (a and β) reacted more than 10⁴ times faster than ethers of the naphthyl benzyl series (a and β). This preference for regioconservation of spin density in the scission process is interpreted in terms of a-bond polarization at the transition state.

Original language	English (US)
Pages (from-to)	2637-2640
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	108
Issue number	10
DOIs	https://doi.org/10.1021/ja00270a022
State	Published - 1986

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "Naphthylmethyl phenyl ethers and naphthyl benzyl ethers were found to undergo scission of the H2C-O bond when treated with radical anions of anthracene or fluoranthene. Under comparable conditions, ethers of the naphthylmethyl phenyl series (a and β) reacted more than 104 times faster than ethers of the naphthyl benzyl series (a and β). This preference for regioconservation of spin density in the scission process is interpreted in terms of a-bond polarization at the transition state.",

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AU - Guthrie, Robert D.

PY - 1986

Y1 - 1986

N2 - Naphthylmethyl phenyl ethers and naphthyl benzyl ethers were found to undergo scission of the H2C-O bond when treated with radical anions of anthracene or fluoranthene. Under comparable conditions, ethers of the naphthylmethyl phenyl series (a and β) reacted more than 104 times faster than ethers of the naphthyl benzyl series (a and β). This preference for regioconservation of spin density in the scission process is interpreted in terms of a-bond polarization at the transition state.

AB - Naphthylmethyl phenyl ethers and naphthyl benzyl ethers were found to undergo scission of the H2C-O bond when treated with radical anions of anthracene or fluoranthene. Under comparable conditions, ethers of the naphthylmethyl phenyl series (a and β) reacted more than 104 times faster than ethers of the naphthyl benzyl series (a and β). This preference for regioconservation of spin density in the scission process is interpreted in terms of a-bond polarization at the transition state.

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Electron Apportionment in Cleavage of Radical Anions. 2. Naphthylmethyl Phenyl Ethers vs. Naphthyl Benzyl Ethers

Abstract

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