Ionic vs. Free-Radical Additions with Opportunity for Phenyl Migration. Solvent Effects

Alfred Hassner; J. Stephen Teeter

doi:10.1021/jo00814a031

Ionic vs. Free-Radical Additions with Opportunity for Phenyl Migration. Solvent Effects

Alfred Hassner, J. Stephen Teeter

University of Colorado Boulder

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

12 Scopus citations

Abstract

Addition of bromine azide to 3,3,3-triphenylpropene (1) proceeds with phenyl migration under ionic conditions (major product, 7) but without phenyl migration under free-radical conditions (major product, 9). The two products resulting from bromination of 1 were shown to derive from simultaneous ionic and free-radical addition processes. Addition of BrN₃ to 3,3-diphenylpropene (10) in polar solvents also proceeds with phenyl migration. The regiochemistry indicates steric control in the BrN3 addition. Solvent effects of a different nature were observed during phenyl migration in the IN₃ addition to 3,3-diphenylpropene (10) and are interpreted in conjunction with three-membered-ring iodonium ion opening.

Original language	English
Pages (from-to)	2176-2180
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	36
Issue number	15
DOIs	https://doi.org/10.1021/jo00814a031
State	Published - 1 Jul 1971
Externally published	Yes

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10.1021/jo00814a031

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abstract = "Addition of bromine azide to 3,3,3-triphenylpropene (1) proceeds with phenyl migration under ionic conditions (major product, 7) but without phenyl migration under free-radical conditions (major product, 9). The two products resulting from bromination of 1 were shown to derive from simultaneous ionic and free-radical addition processes. Addition of BrN3 to 3,3-diphenylpropene (10) in polar solvents also proceeds with phenyl migration. The regiochemistry indicates steric control in the BrN3 addition. Solvent effects of a different nature were observed during phenyl migration in the IN3 addition to 3,3-diphenylpropene (10) and are interpreted in conjunction with three-membered-ring iodonium ion opening.",

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N2 - Addition of bromine azide to 3,3,3-triphenylpropene (1) proceeds with phenyl migration under ionic conditions (major product, 7) but without phenyl migration under free-radical conditions (major product, 9). The two products resulting from bromination of 1 were shown to derive from simultaneous ionic and free-radical addition processes. Addition of BrN3 to 3,3-diphenylpropene (10) in polar solvents also proceeds with phenyl migration. The regiochemistry indicates steric control in the BrN3 addition. Solvent effects of a different nature were observed during phenyl migration in the IN3 addition to 3,3-diphenylpropene (10) and are interpreted in conjunction with three-membered-ring iodonium ion opening.

AB - Addition of bromine azide to 3,3,3-triphenylpropene (1) proceeds with phenyl migration under ionic conditions (major product, 7) but without phenyl migration under free-radical conditions (major product, 9). The two products resulting from bromination of 1 were shown to derive from simultaneous ionic and free-radical addition processes. Addition of BrN3 to 3,3-diphenylpropene (10) in polar solvents also proceeds with phenyl migration. The regiochemistry indicates steric control in the BrN3 addition. Solvent effects of a different nature were observed during phenyl migration in the IN3 addition to 3,3-diphenylpropene (10) and are interpreted in conjunction with three-membered-ring iodonium ion opening.

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Ionic vs. Free-Radical Additions with Opportunity for Phenyl Migration. Solvent Effects

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