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Chemical Compound Review

AG-G-31564     cyclohexa-1,4-diene

Synonyms: ACMC-209snj, CHEBI:37611, ANW-41405, CTK2F4672, KSC354M7F, ...
 
 
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High impact information on EINECS 211-043-1

  • [Mn(III)H(3)1(O)](2-) and [Fe(III)H(3)1(O)](2-) react with other organic substrates containing C-H bonds less than 80 kcal/mol, including 9,10-dihydroanthracene and 1,4-cyclohexadiene to produce [M(II)H(3)1(OH)](2-) and the appropriate dehydrogenated product in yields of greater than 80% [1].
  • Both the onset peaks and the activation energies determined by differential scanning calorimetry (DSC; either in neat enediynes or in their solutions in 10.6 M 1,4-cyclohexadiene (1,4-CHD)) strongly overestimate the reactivity of 1,2-diethynylbenzene, suggesting that DSC cannot be taken as a reliable indicator of enediyne reactivity [2].
  • Evidence of a photochemically initiated diradical cyclization pathway is proposed on the basis of (i) hydrogen abstraction from reaction with 1,4-cyclohexadiene (1,4-CHD) and (ii) the observation of 1,4-addition of benzene (solvent) [3].
  • With limiting fluxes of protons to control the rate of formation of HO2. from O2.-, the rate of decay of HO2. is enhanced by reaction with the allylic hydrogens of excess 1,4-cyclohexadiene (RH) [4].
  • Carbon and oxygen near-edge X-ray absorption fine structure (NEXAFS) spectra of 1,4-cyclohexadiene, p-benzoquinone, norbornadiene, norbornadienone, and cis-cis-[4,4,2]propella-3,8-diene-11,12-dione were calculated by means of Hartree-Fock and hybrid density functional theory using the static-exchange (STEX) approximation [5].
 

Associations of EINECS 211-043-1 with other chemical compounds

  • We show that the X-ray absorption spectrum of 1,4-cyclohexadiene exhibits some particular spectral structures in the discrete energy region that evidence diene through-bond orbital interaction, whereas absorption peaks are identified in the norbornadiene and norbornadienone spectra that indicate effective through-space orbital interactions [5].
  • Hydrogen atom abstraction of 1,4-cyclohexadiene and tert-butyl substituted phenols by the GAO model complexes proceeds very efficiently to give benzene and the corresponding phenoxyl radical or its C-C coupling dimer as the oxidation products, respectively [6].
  • A laser-induced fluorescence spectrum was observed in the 500-560 nm region when a mixture of 1,4-cyclohexadiene and oxalyl chloride was photolyzed at 193 nm [7].

References

  1. Monomeric MnIII/II and FeIII/II complexes with terminal hydroxo and oxo ligands: probing reactivity via O-H bond dissociation energies. Gupta, R., Borovik, A.S. J. Am. Chem. Soc. (2003) [Pubmed]
  2. Ortho effect in the Bergman cyclization: comparison of experimental approaches and dissection of cycloaromatization kinetics. Zeidan, T.A., Kovalenko, S.V., Manoharan, M., Alabugin, I.V. J. Org. Chem. (2006) [Pubmed]
  3. 1,4-Addition of benzene to a dihydrocyclopent[a]indene diradical: synthesis and DFT study. Marsella, M.J., Yoon, K., Estassi, S., Tham, F.S., Borchardt, D.B., Bui, B.H., Schreiner, P.R. J. Org. Chem. (2005) [Pubmed]
  4. Reactivity of perhydroxyl (HOO.) with 1,4-cyclohexadiene (model for allylic groups in biomembranes). Sawyer, D.T., McDowell, M.S., Yamaguchi, K.S. Chem. Res. Toxicol. (1988) [Pubmed]
  5. Probing weak molecular orbital interactions in non-conjugated diene molecules by means of near-edge X-ray absorption spectroscopy. Felicíssimo, V.C., Cesar, A., Luo, Y., Gel'mukhanov, F., Agren, H. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
  6. Hydrogen atom abstraction by Cu(II)- and Zn(II)-phenoxyl radical complexes, models for the active form of galactose oxidase. Taki, M., Kumei, H., Itoh, S., Fukuzumi, S. J. Inorg. Biochem. (2000) [Pubmed]
  7. Laser-induced fluorescence of cyclohexadienyl (c-C(6)H(7)) radical in the gas phase. Imamura, T., Zhang, W., Horiuchi, H., Hiratsuka, H., Kudo, T., Obi, K. The Journal of chemical physics. (2004) [Pubmed]
 
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