Stereochemie aliphatischer Carbokationen, 10. Umlagerungen von 3‐Methyl‐2‐butyl‐Kationen

Kirmse, Wolfgang; Krause, Detlef

doi:10.1002/cber.19751080609

Cited by 15 publications

(2 citation statements)

References 18 publications

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“…This is a strong evidence for the transient formation of a carbenium ion as the isotope effect for the 1,2-H-shift is known to be very small in carbenium ions. It has been indeed previously demonstrated that a 1,2-H-shift isotope effect of k H / k D = 1.2–1.3 was obtained starting from 2-butyldiazonium ion 225 , which is known to decay via a carbenium ion [ 149 – 150 ].…”

Section: Reviewmentioning

confidence: 99%

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

Fernandes¹,

Panossian²,

Michelet³

et al. 2021

Beilstein J. Org. Chem.

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“The extraordinary instability of such an “ion” accounts for many of the peculiarities of organic reactions” – Franck C. Whitmore (1932). This statement from Whitmore came in a period where carbocations began to be considered as intermediates in reactions. Ninety years later, pointing at the strong knowledge acquired from the contributions of famous organic chemists, carbocations are very well known reaction intermediates. Among them, destabilized carbocations – carbocations substituted with electron-withdrawing groups – are, however, still predestined to be transient species and sometimes considered as exotic ones. Among them, the CF3-substituted carbocations, frequently suggested to be involved in synthetic transformations but rarely considered as affordable intermediates for synthetic purposes, have long been investigated. This review highlights recent and past reports focusing on their study and potential in modern synthetic transformations.

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Section: Reviewmentioning

confidence: 99%

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

Fernandes¹,

Panossian²,

Michelet³

et al. 2021

Beilstein J. Org. Chem.

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“…2-Methyl-4-phenyl-2-butanol (13), the product of a sequential Ph,H shift, was formed in the solvolysis of 2, but 3methyl-1 -phenyl-1 -butanol (15) was not obtained. The absence of 15 constitutes additional evidence against the open cation 9 which would be expected to undergo 1,2-H shifts to give 10 and 12 with comparable case.…”

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confidence: 99%

Sequential rearrangements via bridged carbocations

Kirmse¹,

GUENTHER²

1978

J. Am. Chem. Soc.

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Stickstoff als Abgangsgruppe: Aliphatische Diazonium-Ionen

Kirmse

1976

Angew. Chem.

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Stereochemie aliphatischer Carbokationen, 10. Umlagerungen von 3‐Methyl‐2‐butyl‐Kationen

Cited by 15 publications

References 18 publications

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

Sequential rearrangements via bridged carbocations

Stickstoff als Abgangsgruppe: Aliphatische Diazonium-Ionen

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Stereochemie aliphatischer Carbokationen, 10. Umlagerungen von 3‐Methyl‐2‐butyl‐Kationen

Cited by 15 publications

References 18 publications

CF3-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

CF3-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

Sequential rearrangements via bridged carbocations

Stickstoff als Abgangsgruppe: Aliphatische Diazonium-Ionen

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Product

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CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry