Photoisomerizations of 2-methylphenylcyclopropanes to 4-phenylbutenes.  Stereochemistry at the benzylic carbon

Mazzocchi, Paul H.; Lustig, Robert S.

doi:10.1021/ja00802a058

Cited by 8 publications

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“…Experiments on the stereochemistry at the migration terminus further elucidate the mechanism of this reaction. 23…”

Section: Isotope Effects and Stereochemistrymentioning

confidence: 99%

Photoisomerizations of 2-methylphenylcyclopropanes. Isotope effects and stereochemistry

Mazzocchi¹,

Lustig²

1973

J. Org. Chem.

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from an authentic sample.12 The surprisingly efficient lactonization-migration step13 is an intriguing aspect of this synthesis and is the subject of current investigation. The utility of this approach in preparing further analogs of rosenonolactone, e.g., the 11/3-hydroxy derivative, Rosein III,9 is also under examination. Supplementary Material Available.-Complete experimental details on all compounds described in this communication will appear following these pages in the microfilm edition of this volume of the journal. Photocopies of the supplementary material from this paper only or microfiche (105 X 148 mm, 20 X reduction, negatives) containing all of the supplementary material for the papers in this issue may be obtained from the Journals Department, American Chemical Society, 1155 16th St., N.W., Washington, D. C. 20036. Remit check or money order for 83.00 for photocopy or 82.00 for microfiche, referring to code number JOC-73-4090.

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“…Experiments on the stereochemistry at the migration terminus further elucidate the mechanism of this reaction. 23…”

Section: Isotope Effects and Stereochemistrymentioning

confidence: 99%

Photoisomerizations of 2-methylphenylcyclopropanes. Isotope effects and stereochemistry

Mazzocchi¹,

Lustig²

1973

J. Org. Chem.

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Radical Cation/Anion and Neutral Radicals: A Comparison

Hancock

Tanko

2012

Encyclopedia of Radicals in Chemistry, Biology and Materials

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This article examines similarities between radical and radical ion reactions. Radicals and radical ions have worked there way into almost every facet of mainstream chemistry over the past 60 years. The importance as well as usefulness now associated with the reactions of radicals is in stark contrast to their prior role as poorly understood scapegoat molecules often blamed for failed reactions. The processes discussed herein demonstrate two critically important concepts to the radical chemist: (i) kinetic studies are an excellent and versatility applicable tool to determine mechanistic data for chemical reactions and (ii) published mechanistic data for more thoroughly studied radical processes have provided and continue to provide key insight into the factors governing reactivity and mechanism of their charge bearing counterparts.

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ChemInform Abstract: PHOTOISOMERIZATIONS OF 2 METHYLPHENYLCYCLOPROPANES TO 4‐PHENYLBUTENES, STEREOCHEMISTRY AT THE BENZYLIC CARBON

Mazzocchi¹,

Lustig²

1973

Chemischer Informationsdienst

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Photoisomerizations of 2-methylphenylcyclopropanes to 4-phenylbutenes. Stereochemistry at the benzylic carbon

Cited by 8 publications

References 0 publications

Photoisomerizations of 2-methylphenylcyclopropanes. Isotope effects and stereochemistry

Photoisomerizations of 2-methylphenylcyclopropanes. Isotope effects and stereochemistry

Radical Cation/Anion and Neutral Radicals: A Comparison

ChemInform Abstract: PHOTOISOMERIZATIONS OF 2 METHYLPHENYLCYCLOPROPANES TO 4‐PHENYLBUTENES, STEREOCHEMISTRY AT THE BENZYLIC CARBON

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