Oxidation of arylcyclopropanes in solution and in a zeolite: Structure and rearrangement of the phenylcyclopropane radical cation

Heinz D. Roth; Torsten Herbertz; Prasad S. Lakkaraju; Gregory Sluggett; Nicholas J. Turro

doi:10.1021/jp991619u

Oxidation of arylcyclopropanes in solution and in a zeolite: Structure and rearrangement of the phenylcyclopropane radical cation

Heinz D. Roth, Torsten Herbertz, Prasad S. Lakkaraju, Gregory Sluggett, Nicholas J. Turro

School of Arts and Sciences, Chemistry & Chemical Biology

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

16 Scopus citations

Abstract

The structure of phenylcyclopropane radical cation (1^·+, R = H) is derived from CIDNP effects observed during the electron transfer reaction of 1 with chloranil. This species is an example of an elusive structure type. The secondary cyclopropane protons show significantly divergent hyperfine coupling constants due to an unprecedented stereoelectronic effect. Incorporation into a redox-active pentasil zeolite (Na-ZSM-5) converts 1 or its p-methoxy derivative (1, R = OCH₃) to trans-propenylarene radical cations (2^·+, R = H, OCH₃).

Original language	English (US)
Pages (from-to)	11350-11354
Number of pages	5
Journal	Journal of Physical Chemistry A
Volume	103
Issue number	51
DOIs	https://doi.org/10.1021/jp991619u
State	Published - Dec 23 1999

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry

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title = "Oxidation of arylcyclopropanes in solution and in a zeolite: Structure and rearrangement of the phenylcyclopropane radical cation",

abstract = "The structure of phenylcyclopropane radical cation (1·+, R = H) is derived from CIDNP effects observed during the electron transfer reaction of 1 with chloranil. This species is an example of an elusive structure type. The secondary cyclopropane protons show significantly divergent hyperfine coupling constants due to an unprecedented stereoelectronic effect. Incorporation into a redox-active pentasil zeolite (Na-ZSM-5) converts 1 or its p-methoxy derivative (1, R = OCH3) to trans-propenylarene radical cations (2·+, R = H, OCH3).",

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doi = "10.1021/jp991619u",

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T1 - Oxidation of arylcyclopropanes in solution and in a zeolite

T2 - Structure and rearrangement of the phenylcyclopropane radical cation

AU - Roth, Heinz D.

AU - Herbertz, Torsten

AU - Lakkaraju, Prasad S.

AU - Sluggett, Gregory

AU - Turro, Nicholas J.

PY - 1999/12/23

Y1 - 1999/12/23

N2 - The structure of phenylcyclopropane radical cation (1·+, R = H) is derived from CIDNP effects observed during the electron transfer reaction of 1 with chloranil. This species is an example of an elusive structure type. The secondary cyclopropane protons show significantly divergent hyperfine coupling constants due to an unprecedented stereoelectronic effect. Incorporation into a redox-active pentasil zeolite (Na-ZSM-5) converts 1 or its p-methoxy derivative (1, R = OCH3) to trans-propenylarene radical cations (2·+, R = H, OCH3).

AB - The structure of phenylcyclopropane radical cation (1·+, R = H) is derived from CIDNP effects observed during the electron transfer reaction of 1 with chloranil. This species is an example of an elusive structure type. The secondary cyclopropane protons show significantly divergent hyperfine coupling constants due to an unprecedented stereoelectronic effect. Incorporation into a redox-active pentasil zeolite (Na-ZSM-5) converts 1 or its p-methoxy derivative (1, R = OCH3) to trans-propenylarene radical cations (2·+, R = H, OCH3).

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JF - Journal of Physical Chemistry A

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ER -

Oxidation of arylcyclopropanes in solution and in a zeolite: Structure and rearrangement of the phenylcyclopropane radical cation

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