Unexpected Differences in the α-Halogenation and Related Reactivity of Sulfones with Perhaloalkanes in KOH-t-BuOH

CY Meyers, R Chan-Yu-King, DH Hua…

Index: Meyers, Cal Y.; Chan-Yu-King, Roch; Hua, Duy H.; Kolb, Vera M.; Matthews, Walter S.; Parady, Thomas E.; Horii, Toyokazu; Sandrock, Paul B.; Hou, Yuqing; Xie, Songwen Journal of Organic Chemistry, 2003 , vol. 68, # 2 p. 500 - 511

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Citation Number: 8

Abstract

Most alkyl phenyl sulfones are readily α-chlorinated with CCl4 and α-brominated with CBrCl3 in KOH-t-BuOH via radical-anion radical pair (RARP) reactions. While isopropyl mesityl sulfone (4) is easily α-chlorinated with CCl4, it was completely recovered when treated with the more reactive CBrCl3. Subsequent investigations showed the latter result to be due to the poor acidity of 4 together with the rapid depletion of CBrCl3 and KOH by ...