10372
J. Am. Chem. Soc. 1998, 120, 10372-10378
Solvent Effects on Carbocation-Nucleophile Combination Reactions: A Comparison of π-Nucleophilicity in Aqueous and Organic Solvents John P. Richard,*,1 Paul Szymanski, and Kathleen B. Williams Contribution from the Department of Chemistry, UniVersity at Buffalo, SUNY, Buffalo, New York 14260-3000 ReceiVed May 27, 1998
Abstract: The following selectivities are reported for partitioning of the R-(N,N-dimethylthiocarbamoyl)-4methoxybenzyl carbocation 1+ between nucleophilic addition of π-nucleophiles and a solvent of 50:50 (v:v) acetonitrile/water at 25 °C (nucleophile, kNu/ks): pyrrole, 23 M-1; 2-methoxythiophene, ≈2 M-1. No nucleophile adducts (
