Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Aroyl Arenesulfonyl Peroxides. V. Mechanisms of the Reactions of Benzoyl p-Toluenesulfonyl Peroxide with Several Nucleophiles
Ryuki HisadaMichio KobayashiHiroshi Minato
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1972 Volume 45 Issue 7 Pages 2035-2039

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Abstract

Reactions of benzoyl p-toluenesulfonyl peroxide (BTP) with several nucleophiles were investigated. The reaction with triphenylphosphine gave benzoyl p-toluenesulfonate and triphenylphosphine oxide, that with diphenyl sulfide gave benzoyl p-toluenesulfonate and diphenyl sulfoxide, and that with p-tolylmagnesium bromide gave p-toluenesulfonate and benzoic acid. In the reaction of BTP[carbonyl-18O] with triphenylphosphine, 88% of carbonyl oxygen-18 was retained as the carbonyl oxygen of the benzoyl p-toluenesulfonate formed, whereas in the reaction of BTP[carbonyl-18O] with diphenyl sulfide only 58% of the label in the starting peroxide was found in the carbonyl oxygen of the benzoyl p-toluenesulfonate formed. In the reaction of BTP[sulfonyl-18O] with p-tolylmagnesium bromide, it was found that the two sulfonyl oxygens of BTP were completely retained in the two sulfonyl oxygens of the p-tolyl p-toluenesulfonate formed. Possible mechanisms of these reactions are discussed.

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