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Uspekhi Khimii, 1975, Volume 44, Issue 5, Pages 793–867 (Mi rcr2797)  

This article is cited in 253 scientific papers (total in 253 papers)

Carbocations and Electrophilic Reactions

G. A. Olah

Faculty of Chemistry, Case Western Reserve University, USA
Full-text PDF Citations (253)
Abstract: The general concept of carbocations encompasses all cations of carbon containing compounds which can be differentiated into two distinct classes: trivalent ("classical") carbenium ions and pentacoordinated ("nonclassical") carbonium ions. In this paper the preparation and structural study (by NMR, IR, Raman and ESCA spectroscopy) of stable carbenium ions and carbonium ions are discussed. As is well known, trivalent carbenium ions play an important role in electrophilic reactions of π- and n-donor systems. Similarly, pentacoordinated carbonium ions are the key to electrophilic reactions of σ-donor systems (single bonds). The ability of single bonds to act as σ-donor lies in their ability to form carbonium ions via triangular two electron, three-center bond formation. Consequently there seems to be no principle difference between the electrophilic reactions of π- and σ-bonds except that the former react more easily, even with weak electrophiles, whereas the latter necessitate more severe conditions. The role of carbocations in electrophilic reactions of π- and σ-donor systems is discussed.
English version:
Angew. Chem. Int. Ed., 1973, Volume 12, Issue 3, Pages 173–212
DOI: https://doi.org/10.1002/anie.197301731
Document Type: Article
UDC: 547.16
Language: Russian


Citation: G. A. Olah, “Carbocations and Electrophilic Reactions”, Usp. Khim., 44:5 (1975), 793–867; Angew. Chem. Int. Ed., 12:3 (1973), 173–212
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  • https://www.mathnet.ru/eng/rcr2797
  • https://doi.org/10.1002/anie.197301731
  • https://www.mathnet.ru/eng/rcr/v44/i5/p793
  • This publication is cited in the following 253 articles:
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