On the 6-e ndo Selectivity in 4-Penten-1-oxyl Radical Cyclizations

…, R Kneuer, C Rummey, G Bringmann

Index: Hartung, Jens; Kneuer, Rainer; Rummey, Christian; Bringmann, Gerhard Journal of the American Chemical Society, 2004 , vol. 126, # 38 p. 12121 - 12129

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Citation Number: 31

Abstract

Regioselectivities in cyclizations of 4-substituted 4-penten-1-oxyl radicals have been investigated in a combined experimental and computational study (density functional theory). The progressive increase of the 6-endo-trig selectivity along the series of 4- substituents H< CH3< C (CH3) 3< C6H5 has been interpreted to originate from a balance between strain and FMO interactions. Torsional strain, which is associated with ...