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Volumn 119, Issue 36, 1997, Pages 8425-8431

[1.1]Paracyclophane. Photochemical generation from the corresponding bis(Dewar benzene) derivative and theoretical study of its structure and strain energy

Author keywords

[No Author keywords available]

Indexed keywords

PARACYCLOPHANE DERIVATIVE;

EID: 0030869321     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9715253     Document Type: Article
Times cited : (38)

References (63)
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  • 5
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    • (1990) Cyclophan-Chemie
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    • and references cited therein
    • Paracyclophane and its derivatives so far prepared are not sufficiently stable to permit their isolation, but persist for a fairly long time in dilute solution in the absence of air at ambient temperature. Van Es, D. S.; de Kanter, F. J. J.; de Wolf, W. H.; Bickelhaupt, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2553-2555 and references cited therein.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 2553-2555
    • Van Es, D.S.1    De Kanter, F.J.J.2    De Wolf, W.H.3    Bickelhaupt, F.4
  • 37
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    • Ger. Patent 950 285, 1956
    • (b) Jones, D. G. Ger. Patent 950 285, 1956; Chem. Abstr. 1959, 53, 17926d.
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  • 38
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    • V. 3.0; Cambridge Scientific Computing: Cambridge, MA
    • The calculations were performed with Chem3D Plus, V. 3.0; Cambridge Scientific Computing: Cambridge, MA, 1990.
    • (1990) Chem3D Plus
  • 45
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    • (b) Kunz, H. Chem. Ber. 1976, 109, 3693-3706.
    • (1976) Chem. Ber. , vol.109 , pp. 3693-3706
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  • 47
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    • note
    • A 5:5:2 mixture of diethyl ether, isopentane, and ethanol.
  • 48
    • 1842279552 scopus 로고    scopus 로고
    • note
    • 4 Thus, the possibility that the observed spectra were due to 2a and 2b, [4]paracyclophane derivatives, is ruled out.
  • 49
    • 1842341815 scopus 로고    scopus 로고
    • note
    • To our knowledge, the photochemical transformation of 1a,b into 21a,b represents the first direct formation of benzene p,p-dimer.
  • 50
    • 1842346648 scopus 로고    scopus 로고
    • note
    • 2h symmetric (vide infra).
  • 51
    • 1842344700 scopus 로고    scopus 로고
    • note
    • 8
  • 53
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    • Rappoport, Z., Ed.; J. Wiley & Sons: Chichester, England
    • (b) Morris, D. G. The Chemistry of Cyclopropyl Group; Rappoport, Z., Ed.; J. Wiley & Sons: Chichester, England, 1987; pp 101-172.
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    • note
    • 16
  • 55
    • 1842280522 scopus 로고    scopus 로고
    • note
    • The sample contained 1a, 21a, and 3a in a ratio of ca. 3:2:300 after the initial irradiation with 254-nm light. Extended irradiation did not bring about an appreciable increase in the proportion of (1a + 21a):3a and only induced the decomposition of the products and 3a.
  • 58
    • 84982056958 scopus 로고
    • A-C of 1b resonate at δ 7.17 (d, J = 1.8 Hz), 6.68 (dd, J = 7.7 and 1.8 Hz), and 6.51 (d, J = 7.7 Hz), respectively. Hopf, H.; Lenich, F. T. Chem. Ber. 1974,107, 1891-1902.
    • (1974) Chem. Ber. , vol.107 , pp. 1891-1902
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    • Revised as Ver. 5.01 by Toyoda, J. for Apple Macintosh
    • Stewart, J. J. P. QCPE Bull. 1989, 9, 10. Hirano, T. JCPE NewsLetter 1989, 1, 36; Revised as Ver. 5.01 by Toyoda, J. for Apple Macintosh.
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    • 6 The insignificant bond alteration in 1a, therefore, is not surprising. We recently observed that significant diatropicity is retained in a [4]paracyclophane derivative, suggesting the sustenance of substantial aromatic ring current in its benzene ring. Okuyama, M.; Tsuji, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1085-1087.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1085-1087
    • Okuyama, M.1    Tsuji, T.2


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