The [3 + 2]- and [5 + 2]-cycloadditions of the cyclohepta-2,4-dienyl cation

Heilmann, Werner; Koschinsky, R.; Mayr, Herbert

doi:10.1021/jo00386a017

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Perezone-type [5 + 2] Cycloaddition Reactions1

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2024

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Cited by 9 publications

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“…Although not directly related to the perezone-type cycloaddition processes, the report of an intermolecular [5 + 2] cycloaddition reaction between cycloheptadienyl chloride 17 and 2-methyl-1-methoxy-1-propene warrants discussion here . When 17 and a vinyl ether are combined in the presence of ZnCl 2 ·OEt 2 , five distinct products are obtained (Scheme ).…”

Section: Perezone-type [5 + 2] Cycloaddition Reactionsmentioning

confidence: 99%

[5 + 2] Cycloaddition Reactions in Organic and Natural Product Synthesis

2012

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Section: Perezone-type [5 + 2] Cycloaddition Reactionsmentioning

confidence: 99%

[5 + 2] Cycloaddition Reactions in Organic and Natural Product Synthesis

2012

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[m+n(+…)] Cycloaddition

2010

Comprehensive Organic Name Reactions and Reagents

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The cycloaddition reaction is an important reaction in organic synthesis, in which two or more molecules combine and form new ring structures, along with the formation of multiple bonds and multiple stereogenic centers in a single step. Besides this, cycloadditions are also considered the right choice when high regioselectivities, chemoselectivities and stereoselectivities are concerned. The present study represents various types of cycloadditions reactions and their mechanism currently used in organic syntheses.

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Dearomative Intramolecular meta‐Thermocycloadditions of Benzene Rings via Wheland Intermediates

Liu,

Xu,

Liu

et al. 2024

Angewandte Chemie

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Dearomative cycloadditions are powerful synthetic transformations utilizing aromatic compounds for cycloaddition reactions. They have been extensively applied to the synthesis of biologically relevant compounds not only because of the complexity generated from simplicity but also the atom‐ and step‐economy. For the most studied yet challenging benzene ring systems, ortho‐ and para‐cycloadditions have been realized both photochemically and thermally, while the meta‐cycloadditions are still limited to the photochemical processes tracing back to the 1960s. Herein, we for the first time realized the thermal cycloadditions of benzene rings with alkenes in a meta fashion via Wheland intermediates. A broad spectrum of readily available C(sp2)‐rich aniline‐tethered enynes were transformed into C(sp3)‐rich 3D complex polycyclic architectures simply by stirring in TFA. Moreover, the reaction could be performed in gram‐scales and the products could be diversely elaborated.

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The [3 + 2]- and [5 + 2]-cycloadditions of the cyclohepta-2,4-dienyl cation

Cited by 9 publications

References 0 publications

[5 + 2] Cycloaddition Reactions in Organic and Natural Product Synthesis

[5 + 2] Cycloaddition Reactions in Organic and Natural Product Synthesis

[m+n(+…)] Cycloaddition

Dearomative Intramolecular meta‐Thermocycloadditions of Benzene Rings via Wheland Intermediates

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