Naphthyl‐Substituted Carbocations: From <i>peri</i> Interaction to Cyclization

Dyker, Gerald; Hagel, Marcel; Henkel, Gerald; Köckerling, Martin

doi:10.1002/ejoc.200800124

Cited by 7 publications

(1 citation statement)

References 24 publications

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“…The Dyker group were interested in naphthyl-substituted triarylmethane compounds due to their potential as indicators and reported the synthesis of some naphtho-annulated triarylmethanes (Scheme 17). 76 The synthesis of model compound 82 was achieved by lithiation of the peri-substituted 1-iodo-8-methoxynaphthalene (83) followed by addition to 5-dibenzosuberenone (1)…”

Section: Syn Thesismentioning

confidence: 99%

The Dibenzosuberenone Scaffold as a Privileged Substructure: From Synthesis to Application

2017

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Numerous studies on dibenzosuberenones, especially on 5-dibenzosuberenones, have emerged in recent years. This review focuses on the chemistry of dibenzosuberenones, including their synthesis and applications, which are currently used as tools by the synthetic and biological communities.1 Introduction2 5-Dibenzosuberenone (5H-Dibenzo[a,d]cyclohepten-5-one)2.1 Synthesis of 5-Dibenzosuberenone2.2 Reactions of 5-Dibenzosuberenone3 5H-Dibenzo[a,c]cyclohepten-5-one3.1 Synthesis of 5H-Dibenzo[a,c]cyclohepten-5-one3.2 Reactions of 5H-Dibenzo[a,c]cyclohepten-5-one4 6H-Dibenzo[a,c]cyclohepten-6-one and 10H-Dibenzo[a,d]cyclohepten-10-one4.1 Generation and Trapping of 6H-Dibenzo[a,c]cyclohepten-6-one and 10H-Dibenzo[a,d]cyclohepten-10-one5 Dibenzocycloheptenediones5.1 Synthesis of Dibenzocycloheptenediones5.2 Reactions of Dibenzocycloheptenediones6 Conclusion

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Section: Syn Thesismentioning

confidence: 99%

The Dibenzosuberenone Scaffold as a Privileged Substructure: From Synthesis to Application

2017

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Carbocations

McClelland

2011

Organic Reaction Mechanisms · 2008

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[Co₂(CO)₆(Alkynyl)] Complexes of Dibenzosuberyl and Dibenzosuberenyl Carbocations: Dibenzotropylium or Dibenzoheptafulvene?

et al. 2016

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The reaction of dibenzo[a,d]cycloheptan‐5‐one (dibenzosuberone) and dibenzo[a,d]cyclohept‐10‐en‐5‐one (dibenzosuberenone) with aryl‐ or trimethylsilylacetylides led to the formation of the corresponding alkynyldibenzosuberols and alkynyldibenzosuberenols. Treatment with dicobalt octacarbonyl and then with bis(diphenylphosphino)methane (dppm) furnished the corresponding [Co2(CO)4(dppm)(alkynol)] clusters 25 and 29. Upon protonation with HBF4 at 203 K to generate the relevant cobalt‐stabilised cations, the dibenzosuberyl system 30 exhibited fluxionality such that the cation migrated between cobalt centres. Variable‐temperature 31P NMR spectroscopy revealed a barrier of approximately 12.5 kcal mol−1. In contrast, in the supposedly aromatic [Co2(CO)4(dppm)(dibenzosuberenyl)]+ cation (31), which would be expected to have less need of cobalt stabilisation, the barrier was too high to be measured experimentally, but is certainly in excess of 16 kcal mol−1. These data were rationalised by DFT calculations on the structures and energies of the relevant ground states and transition states, which suggested that the nonplanar alkynyldibenzosuberenyl moiety in 31 is better regarded as a neutral dibenzoheptafulvene coordinated to a cationic alkynyl–dicobalt cluster. The question of the bonding of both aromatic and antiaromatic cations to alkyne–dicobalt clusters is considered, and it is proposed that their stabilities, when complexed, parallel the inversion of (4n+2) π and 4n π systems seen under photochemical conditions.

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Naphthyl‐Substituted Carbocations: From peri Interaction to Cyclization

Cited by 7 publications

References 24 publications

The Dibenzosuberenone Scaffold as a Privileged Substructure: From Synthesis to Application

The Dibenzosuberenone Scaffold as a Privileged Substructure: From Synthesis to Application

Carbocations

[Co₂(CO)₆(Alkynyl)] Complexes of Dibenzosuberyl and Dibenzosuberenyl Carbocations: Dibenzotropylium or Dibenzoheptafulvene?

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Naphthyl‐Substituted Carbocations: From peri Interaction to Cyclization

Cited by 7 publications

References 24 publications

The Dibenzosuberenone Scaffold as a Privileged Substructure: From Synthesis to Application

The Dibenzosuberenone Scaffold as a Privileged Substructure: From Synthesis to Application

Carbocations

[Co2(CO)6(Alkynyl)] Complexes of Dibenzosuberyl and Dibenzosuberenyl Carbocations: Dibenzotropylium or Dibenzoheptafulvene?

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[Co₂(CO)₆(Alkynyl)] Complexes of Dibenzosuberyl and Dibenzosuberenyl Carbocations: Dibenzotropylium or Dibenzoheptafulvene?