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Volumn 121, Issue 19, 1999, Pages 4589-4597

Generation, spectroscopic characterization, and reactions of 3,4- benzotropone. Distinctive photochemical behavior of 6,7- benzobicyclo[3.2.0]hepta-3,6-dien-2-one in rigid glass at low temperature and in fluid solution

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKENE; BENZENE; BICYCLO COMPOUND; ETHER DERIVATIVE; GLASS; HYDROCARBON; MALEIC ANHYDRIDE; TROPONE DERIVATIVE;

EID: 0033583757     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984348u     Document Type: Article
Times cited : (17)

References (67)
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    • max at 355, 374, 395, 420, 442, 463, 488, and 523 nm in methylcyclohexane/isopentane (4:1) and at 352, 370, 388, 430 (sh), 447, 470, and 492 nm in ethanol. The bathochromic shifts of the absorption bands in the less polar former solvent suggest that 1 may be less polarized in the excited state than in the ground state: Bayliss, N. S.; McRae, E. G. J. Phys. Chem. 1954, 58, 1002.
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    • Bayliss, N.S.1    McRae, E.G.2
  • 23
    • 0001009707 scopus 로고
    • For acidity constants of carboxylic acids in organic solvents, see: (a) Calder, G. V.; Barton, T. J. J. Chem. Educ. 1971, 48, 338.
    • (1971) J. Chem. Educ. , vol.48 , pp. 338
    • Calder, G.V.1    Barton, T.J.2
  • 31
    • 0002228091 scopus 로고
    • Stewart, J. J. P. QCPE Bull. 1989, 9, 10. Hirano, T. JCPE NewsLett. 1989, 1, 36; Revised as Ver. 5.01 by Toyoda, J., for Apple Macintosh.
    • (1989) QCPE Bull. , vol.9 , pp. 10
    • Stewart, J.J.P.1
  • 32
    • 0002724863 scopus 로고
    • Revised as Ver. 5.01 by Toyoda, J., for Apple Macintosh
    • Stewart, J. J. P. QCPE Bull. 1989, 9, 10. Hirano, T. JCPE NewsLett. 1989, 1, 36; Revised as Ver. 5.01 by Toyoda, J., for Apple Macintosh.
    • (1989) JCPE NewsLett. , vol.1 , pp. 36
    • Hirano, T.1
  • 35
    • 0007636945 scopus 로고
    • Cyclopentenones bearing a radical stabilizing group at C-5 position undergo α-cleavage to afford the corresponding cyclopropyl ketenes: Agosta, W. C.; Smith, A. B., III J. Am. Chem. Soc. 1971, 93, 5513.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 5513
    • Agosta, W.C.1    Smith A.B. III2
  • 36
    • 0018456257 scopus 로고
    • An activation energy of 18.9 ± 0.2 kcal/mol has been reported for the thermal rearrangement of 5,5-dimethylbenzobicyclo[2.1.0]pent-2-ene to 2,2-dimethylisoindene: Dolbier, W. R., Jr.; Matsui, K.; Dewey, H. J.; Horák, D. V.; Michl, J. J. Am. Chem. Soc. 1979, 101, 2136.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 2136
    • Dolbier, W.R.J.1    Matsui, K.2    Dewey, H.J.3    Horák, D.V.4    Michl, J.5
  • 37
    • 0000109765 scopus 로고
    • Cyclopentenones bearing an aromatic ring at C-4 position undergo di-π-methane rearrangement to yield substituted bicyclo[2.1.0]pentan-2-ones which subsequently undergo spontaneous cycloreversion to ketene derivatives at room temperature: Zimmermann, H. E.; Little, R. D. J. Am. Chem. Soc. 1974, 96, 4623.
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    • Zimmermann, H.E.1    Little, R.D.2
  • 53
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    • note
    • Irradiation of microcrystalline 2 in a KBr pellet resulted in the [2 + 2] photodimerization.
  • 60
    • 0345338086 scopus 로고    scopus 로고
    • note
    • Orverlay analysis (minimization of sum of non-hydrogen atom displacements) was performed on the molecular modeling system CS Chem 3D Pro V. 3.5 (CambridgeSoft Corp.; Cambridge, MA) using the PM3 optimized geometries.
  • 62
    • 0000984860 scopus 로고
    • and references therein
    • For the adiabatic electrocyclic ring-opening of cyclobutenes in their singlet excited states, see: Leigh, W. J.; Postigo, J. A.; Venneri, P. C. J. Am. Chem. Soc. 1995, 117, 7826 and references therein.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 7826
    • Leigh, W.J.1    Postigo, J.A.2    Venneri, P.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.