The Bergman reaction as a synthetic tool: advantages and restrictions

Bowles, Daniel M.; Palmer, Grant J.; Landis, Chad A.; Anthony, John E.

doi:10.1016/s0040-4020(01)00247-2

Cited by 59 publications

(33 citation statements)

References 18 publications

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“…As we have demonstrated in a very recent paper [80], other entirely unexplored cyclization modes of enediyne and enyne-allene substrates are possible, leading to fiveand seven-membered rings [81,82]. These findings bear important implications for materials science and nanoelectronics applications as organic materials (as noted in several other chapters of this book, five-membered rings introduce curvature in PAHs) may be fabricated in a more flexible and predictable way [83]. Also, carbon-rich materials are often built up using structures with varying degrees of polyalkynes moieties or substituents; these structures are typically treated thermally (see Chapters 3,4 and 12) to give the desired materials.…”

Section: Cyclization Reactions Of Polyunsaturated Systemsmentioning

confidence: 55%

Carbon‐rich Compounds: Computational Considerations

Schreiner

2006

Carbon‐Rich Compounds

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Section: Cyclization Reactions Of Polyunsaturated Systemsmentioning

confidence: 55%

Carbon‐rich Compounds: Computational Considerations

Schreiner

2006

Carbon‐Rich Compounds

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“…After the diradical 107 has been generated by the Bergman process, the 1,4-diyl is intercepted by the two a,b-unsaturated ester groups and the tetracyclic product 108 is formed (Scheme 24) [60]. In another example, the hexaacetylene 109 -after deprotection with potassium carbonate in methanol -is subjected to typical Bergman trapping conditions, resulting in the formation of the anthracene derivative 110 [61]. As a third, more complex illustration, the aromatization of the triacetylene 111 may be considered.…”

Section: H Nmr Analysis Of Thismentioning

confidence: 99%

“…As a third, more complex illustration, the aromatization of the triacetylene 111 may be considered. Here, the 1,4-diradical intermediate faces another triple bond as an internal trap, and, after hydrogen transfer from 1,4-cyclohexadiene, the tricyclic allylic alcohol 112 is produced [61].…”

Section: H Nmr Analysis Of Thismentioning

confidence: 99%

From Acetylenes to Aromatics: Novel Routes – Novel Products

Hopf

2002

Modern Arene Chemistry

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Alkynes have been used as precursors for aromatic compounds since Berthelot converted acetylene to benzene in 1867. The review presents new evidence on the mechanism of this first total synthesis of an aromatic compound. Presumably, its last step involves the thermocyclization of hexa-1,3-dien-5-yne to benzene. Trapping experiments as well as the study of derivatives of this highly unsaturated hydrocarbon show that the reaction takes place via isobenzene intermediates (1,2,4-cyclohexatrienes) at lower temperatures. Under high temperature pyrolysis conditions, carbenes as well as radical routes compete with the pericyclic process. In another recent application of acetylenes in the synthesis of aromatic compounds,

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“…The Bergman reaction has been studied extensively over the last decade becoming a useful synthetic reaction [39][40][41][42][43][44][45]. The biradical structure, which results from the cycloaromatisation reaction, has been shown [46][47][48] to be a potent antitumour agent through its interaction with DNA strands.…”

Section: Introductionmentioning

confidence: 99%

Many-body Brillouin–Wigner second-order perturbation theory: an application to the autoaromatisation of hex-3-ene-1,5-diyne (the Bergman reaction)

et al. 2008

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To cite this article: P. Papp , P. Neogrady , P. Mach , J. Pittner , I. Huba[cbreve] & S. Wilson (2008) Many-body Brillouin-Wigner second-order perturbation theory: an application to the autoaromatisation of hex-3-ene-1,5-diyne (the The multireference, state specific, second-order, Brillouin-Wigner perturbation theory is applied to the autoaromatisation of hex-3-ene-1, 5-diyne, the Bergman reaction. Calculations are reported for the reactant (hex-3-ene-1, 5-diyne), the transition state and the product (1, 4-didehydrobenzene). A posteriori modifications are made which, in the case of a single reference function, recover the well-known formula of second-order many-body perturbation theory, i.e. Møller-Plesset (MP2) theory, and in the multireference case can be shown to be equivalent to state-specfic multireference Rayleigh-Schro¨dinger-like perturbation theory. Calculations are performed for a sequence of correlation consistent basis sets and, by extrapolation, complete basis set limits of the energetics of the Bergman reaction are estimated.

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The Bergman reaction as a synthetic tool: advantages and restrictions

Cited by 59 publications

References 18 publications

Carbon‐rich Compounds: Computational Considerations

Carbon‐rich Compounds: Computational Considerations

From Acetylenes to Aromatics: Novel Routes – Novel Products

Many-body Brillouin–Wigner second-order perturbation theory: an application to the autoaromatisation of hex-3-ene-1,5-diyne (the Bergman reaction)

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