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Volumn 120, Issue 44, 1998, Pages 11304-11310

Photochemical generation and methanol trapping of localized 1,3 and 1,4 singlet diradicals derived from a spiroepoxy-substituted cylcopentane 1,3- diyl

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; RADICAL;

EID: 0032508972     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9822761     Document Type: Article
Times cited : (55)

References (65)
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    • and also see ref 8b
    • For delocalized singlet diradicals see Bushby, R. J. J. Chem. Soc., Perkin Trans. 2, 1985, 1211 and also see ref 8b.
    • Acc. Chem. Res.
  • 27
    • 3643133262 scopus 로고    scopus 로고
    • note
    • 2CO is 68 kcal/mol; thus, the sensitized process is energywise feasible.
  • 29
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    • note
    • 1H NMR spectroscopy; the product ratio was ca. 91:9.
  • 30
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    • note
    • Although for the corresponding spirocyclopropane-substituted 1,3 diradical the housane persists (ref 17), the failure to observe the housane 2 derives presumably from the fact that epoxide ring is cleaved ca. 100 times faster than the cyclopropane ring (ref 18).
  • 35
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    • For dipolar character in singlet diradicals see (a) Salem, L.; Row and C. Angew. Chem., Int. Ed. Engl. 1972, 11, 92. (b) Jean, Y.; Salem, L. J. Chem. Soc., Chem. Commun. 1971, 382. (c) Horsley, J.A.; Jean Y., Moser, C.; Salem, L.; Sevens, R. M.; Wright, J. S. J. Am. Chem. Soc. 1972, 94, 279.
    • (1972) Angew. Chem., Int. Ed. Engl. , vol.11 , pp. 92
    • Salem, L.1    Row, C.2
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    • For dipolar character in singlet diradicals see (a) Salem, L.; Row and C. Angew. Chem., Int. Ed. Engl. 1972, 11, 92. (b) Jean, Y.; Salem, L. J. Chem. Soc., Chem. Commun. 1971, 382. (c) Horsley, J.A.; Jean Y., Moser, C.; Salem, L.; Sevens, R. M.; Wright, J. S. J. Am. Chem. Soc. 1972, 94, 279.
    • (1971) J. Chem. Soc., Chem. Commun. , pp. 382
    • Jean, Y.1    Salem, L.2
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    • For dipolar character in singlet diradicals see (a) Salem, L.; Row and C. Angew. Chem., Int. Ed. Engl. 1972, 11, 92. (b) Jean, Y.; Salem, L. J. Chem. Soc., Chem. Commun. 1971, 382. (c) Horsley, J.A.; Jean Y., Moser, C.; Salem, L.; Sevens, R. M.; Wright, J. S. J. Am. Chem. Soc. 1972, 94, 279.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 279
    • Horsley, J.A.1    Jean, Y.2    Moser, C.3    Salem, L.4    Sevens, R.M.5    Wright, J.S.6
  • 42
    • 0006416603 scopus 로고
    • Borden, W. T., Ed.; Wiley-Interscience: New York
    • Platz, M. S. In Diradicals; Borden, W. T., Ed.; Wiley-Interscience: New York, 1982; pp 195-258.
    • (1982) Diradicals , pp. 195-258
    • Platz, M.S.1
  • 43
    • 0037630760 scopus 로고
    • The triplet energy of 1,3-cyclohexadine is 52 kcal/mol (Kellogg, R. E.; Schwenker, R. P. J. Chem. Phys. 1964, 41, 2860); that of 2,3-diazabicyclo[2.2.1]hept-2-ene (DBH) derivatives is ca. 60 kcal/mol (ref 14), and thus the triplet quenching is feasible
    • (1964) J. Chem. Phys. , vol.41 , pp. 2860
    • Kellogg, R.E.1    Schwenker, R.P.2
  • 52
    • 3643119741 scopus 로고    scopus 로고
    • note
    • 10 analogue (-23.0 kcal/mol, ref 31).
  • 61
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    • For stereoelectronic effects on cyclopropane-ring cleavage, see (a) Kochi, J. K.; Krusic, P. J.; Eaton, D. R. J. Am. Chem. Soc. 1969, 91, 1877. (b) Friedrich, E. C. J. Org. Chem. 1969, 34, 528. (c) Friedrich, E. C.; Holmstead, R. L. J. Org. Chem. 1971, 36, 971. (d) Friedrich, E. C.; Holmstead, R. L. J. Org. Chem. 1972, 37, 2546. (e) Reference 20d.
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    • Kochi, J.K.1    Krusic, P.J.2    Eaton, D.R.3
  • 62
    • 3643070738 scopus 로고
    • For stereoelectronic effects on cyclopropane-ring cleavage, see (a) Kochi, J. K.; Krusic, P. J.; Eaton, D. R. J. Am. Chem. Soc. 1969, 91, 1877. (b) Friedrich, E. C. J. Org. Chem. 1969, 34, 528. (c) Friedrich, E. C.; Holmstead, R. L. J. Org. Chem. 1971, 36, 971. (d) Friedrich, E. C.; Holmstead, R. L. J. Org. Chem. 1972, 37, 2546. (e) Reference 20d.
    • (1969) J. Org. Chem. , vol.34 , pp. 528
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  • 63
    • 0001434506 scopus 로고
    • For stereoelectronic effects on cyclopropane-ring cleavage, see (a) Kochi, J. K.; Krusic, P. J.; Eaton, D. R. J. Am. Chem. Soc. 1969, 91, 1877. (b) Friedrich, E. C. J. Org. Chem. 1969, 34, 528. (c) Friedrich, E. C.; Holmstead, R. L. J. Org. Chem. 1971, 36, 971. (d) Friedrich, E. C.; Holmstead, R. L. J. Org. Chem. 1972, 37, 2546. (e) Reference 20d.
    • (1971) J. Org. Chem. , vol.36 , pp. 971
    • Friedrich, E.C.1    Holmstead, R.L.2
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    • For stereoelectronic effects on cyclopropane-ring cleavage, see (a) Kochi, J. K.; Krusic, P. J.; Eaton, D. R. J. Am. Chem. Soc. 1969, 91, 1877. (b) Friedrich, E. C. J. Org. Chem. 1969, 34, 528. (c) Friedrich, E. C.; Holmstead, R. L. J. Org. Chem. 1971, 36, 971. (d) Friedrich, E. C.; Holmstead, R. L. J. Org. Chem. 1972, 37, 2546. (e) Reference 20d.
    • (1972) J. Org. Chem. , vol.37 , pp. 2546
    • Friedrich, E.C.1    Holmstead, R.L.2
  • 65
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    • Reference 20d
    • For stereoelectronic effects on cyclopropane-ring cleavage, see (a) Kochi, J. K.; Krusic, P. J.; Eaton, D. R. J. Am. Chem. Soc. 1969, 91, 1877. (b) Friedrich, E. C. J. Org. Chem. 1969, 34, 528. (c) Friedrich, E. C.; Holmstead, R. L. J. Org. Chem. 1971, 36, 971. (d) Friedrich, E. C.; Holmstead, R. L. J. Org. Chem. 1972, 37, 2546. (e) Reference 20d.
    • J. Am. Chem. Soc.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.