Acyclic 1,2-Induction in Radical Reactions: The Importance of Allylic Strain Effects

Bernd Giese; Michel Bulliard; Heinz-Georg Zeitz

doi:10.1055/s-1991-20751

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Synlett 1991; 1991(6): 425-427
DOI: 10.1055/s-1991-20751

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Acyclic 1,2-Induction in Radical Reactions: The Importance of Allylic Strain Effects

Bernd Giese^* , Michel Bulliard, Heinz-Georg Zeitz

^*Institut für Organische Chemie der Universität Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland

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Publication Date:
07 March 2002 (online)

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The stereoselectivity of hydrogen abstraction by ester-substituted radical 1 [XCH(R²)C????-(R¹)CO₂R] is explained by allylic strain effects. The ratio of threo:erythro products 2:3 depends upon the size of substituents X and R².