COMPETITIVE BINDING OF SUPER-WEAK NUCLEOPHILES IN CARBOCATIONIC-LIKE PROCESSES.

Nikolai S. Zefirov, A. S. Koz'min, V. V. Zhdankin, V. N. Kirin, N. M. Yur'eva, V. D. Sorokin

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Abstract

The variety of carbocationic-like processes (electrophilic additions to olefins, deamination of amines, ring opening of epoxides by action of electrophilic agents and oxydative deiodination of alkyl iodides) in the presence of super-weak nucleophiles, such as ClO** minus //4, CF//3SO** minus //3, FSO** minus //3 and TsO** minus proceeds to give the products of covalent binding of these nucleophiles (perchlorates, triflates, fluorosulfonates and tosylates, correspondingly) with modest up to high yield in spite of the presence of other nucleophiles (AcOH, H//2O, I minus , Br** minus , Cl** minus ). The important mechanistic and synthetic sequences are discussed.

Original languageEnglish (US)
Pages (from-to)195-200
Number of pages6
JournalChemica scripta
Volume22
Issue number4
StatePublished - Jan 1 1983

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    Zefirov, N. S., Koz'min, A. S., Zhdankin, V. V., Kirin, V. N., Yur'eva, N. M., & Sorokin, V. D. (1983). COMPETITIVE BINDING OF SUPER-WEAK NUCLEOPHILES IN CARBOCATIONIC-LIKE PROCESSES. Chemica scripta, 22(4), 195-200.