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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Chemical Compound Review: 

Benzyne     cyclohexa-1,3-dien-5-yne

Synonyms: Arine, benzenediyl, Dehydrobenzene, o-Benzyne, AG-F-59355, ...
 
 
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High impact information on o-Benzyne

  • The dehydrogenation of 2,3-C2B5H7 (6a) to 2,3-C2B5H5 (13a) is estimated to be even less endothermic than those of benzene and 1,2- C2B10H12 (1a) to benzyne and 1,2-C2B10H10 (8a) by more than 21 kcal/mol [1].
  • Preparation of benzyne complexes of group 10 metals by intramolecular suzuki coupling of ortho-metalated phenylboronic esters: molecular structure of the first benzyne-palladium(0) complex [2].
  • Central to the approach employed is the formation of a 7-lithiated-2,4-dialkoxybenzothiazole intermediate obtained via a directed-lithiation/benzyne-mediated cyclization reaction [3].
  • Amination of halobenzenes, which proceeds via the benzyne intermediate (1), has been studied using quantum chemical methods [4].
  • The [2 + 2] cycloadditions of cyclopentyne and benzyne to ethylene are explored at the B3LYP and CASSCF levels, supplemented by CCSD(T) and CAS-MP2 calculations at the stationary points [5].
 

Analytical, diagnostic and therapeutic context of o-Benzyne

  • The optical resolution of trans-2 and trans-3 [60]fullerene bisadducts with an inherent chiral addition pattern, modified by Bingel reaction, cycloaddition by benzyne, Prato reaction, and cycloaddition by o-quinodimethane, was systematically investigated by using chiral HPLC columns (Chiralcel OD and Chiralpak AD) [6].

References

  1. Control of stability through overlap matching: closo-carborynes and closo-silaborynes. Kiran, B., Anoop, A., Jemmis, E.D. J. Am. Chem. Soc. (2002) [Pubmed]
  2. Preparation of benzyne complexes of group 10 metals by intramolecular suzuki coupling of ortho-metalated phenylboronic esters: molecular structure of the first benzyne-palladium(0) complex. Retbøll, M., Edwards, A.J., Rae, A.D., Willis, A.C., Bennett, M.A., Wenger, E. J. Am. Chem. Soc. (2002) [Pubmed]
  3. Synthesis of the marine sponge derived beta2-adrenoceptor agonist S1319. Fairhurst, R.A., Janus, D., Lawrence, A. Org. Lett. (2005) [Pubmed]
  4. Computational study of the amination of halobenzenes and phenylpentazole. A viable route to isolate the pentazolate anion? Carlqvist, P., Ostmark, H., Brinck, T. J. Org. Chem. (2004) [Pubmed]
  5. Competing pathways in the [2 + 2] cycloadditions of cyclopentyne and benzyne. A DFT and ab initio study. Ozkan, I., Kinal, A. J. Org. Chem. (2004) [Pubmed]
  6. Systematic enantiomeric separation of [60]fullerene bisadducts possessing an inherent chiral addition pattern. Nakamura, Y., O-kawa, K., Nishimura, T., Yashima, E., Nishimura, J. J. Org. Chem. (2003) [Pubmed]
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