Canadian journal of chemistry

Enhanced nucleophile selectivity in the photoaddition to styrene. Comparison with the thermal addition

SW Anderson, K Yates

Index: Anderson, Steven W.; Yates, Keith Canadian Journal of Chemistry, 1988 , vol. 66, p. 2412 - 2421

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Citation Number: 7

Abstract

The reactivity-selectivity properties of the sec-phenethyl carbenium ion and its analogues have been examined in binary-aqueous solutions of alcohols (ROH; R= Me, Et, CF3CH2, n- Bu, t-Bu, n-Pr, i-Pr), acetic acid, and in solutions containing external nucleophiles such as thiophenol, ethanethiol, acetate, and benzenesulfinate. Selectivity (S= k (Nuc)/k (H2O)) is observed to be a function of the nucleophile, the ring substituent, thermal or ...