Journal of the American Chemical Society

One-electron chemical reductions of phenylalkylsulfonium salts

P Beak, TA Sullivan

Index: Beak, Peter; Sullivan, Thomas A. Journal of the American Chemical Society, 1982 , vol. 104, # 16 p. 4450 - 4457

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Citation Number: 60

Abstract

Abstract: Twenty-two arylalkylsulfonium salts have been reduced with potassium in graphite in tetrahydrofuran and the sulfide products identified. Two trialkylsulfonium salts did not reduce under these conditions. Comparison of the sulfides from a series of monophenylalkylsulfonium salts reveals a leaving-group propensity of benzyl> secondary> primary> methyl> phenyl in a ratio of 28:(6.0 0.3): 1.0:(0.53 f 0.09):< 0.05. The cleavage ...

~13%

Detail

~4%

~40%

~47%

~67%

~85%

~0%

~31%

~0%

~0%

~83%

Detail

~70%

Detail

~93%

~2%

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