Free radical additions. Part II. Kinetics of free radical additions of bromomalononitrile to alkenes and PMO treatment of the reactivity and regioselectivity

…, HM Bartels, R Dornow, E Drechsel-Grau…

Index: Riemenschneider, K.; Bartels, H. M.; Dornow, R.; Drechsel-Grau, E.; Eichel, W.; et al. Journal of Organic Chemistry, 1987 , vol. 52, # 2 p. 205 - 212

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Citation Number: 36

Abstract

The addition rate of dicyanomethyl (DCM) radicals to 2-methyl-1-pentene (2) was found to be k4=(1.6 h 0.4) X lo6 L. mol-'. s-'. Relative rates (krel) of additions to 11 alkenes were measured. Obviously steric effects do not influence the addition rates with n-alkyl-substituted alkenes. The ln krel values correlate linearly (r= 0.98) with the superdelocalizabtiea, Sp, a measure for binding molecular orbital interactions between the reactants (Fukui). The SiR) ...