메뉴 건너뛰기




Volumn 55, Issue 4, 1999, Pages 885-907

The Norrish type II reaction in the crystalline state: Toward a better understanding of the geometric requirements for γ-hydrogen atom abstraction

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN;

EID: 0033593255     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01019-9     Document Type: Review
Times cited : (114)

References (60)
  • 12
    • 0000339357 scopus 로고
    • Padwa, A., Ed.; Marcel Dekker: New York, Chapter 4
    • (b) Wagner, P.; Park, B-S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Volume 11; Chapter 4.
    • (1991) Organic Photochemistry , vol.11
    • Wagner, P.1    Park, B.-S.2
  • 13
    • 0000584612 scopus 로고
    • Padwa, A., Ed.; Marcel Dekker: New York
    • (a) Wilson, R.M. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1985; Volume 7, pp 339-446;
    • (1985) Organic Photochemistry , vol.7 , pp. 339-446
    • Wilson, R.M.1
  • 15
    • 33947480288 scopus 로고
    • (c) Cyclobutanol products in type II photochemistry were first reported by: Yang, N.C.; Yang, D.H. J. Am. Chem. Soc. 1958, 80, 2913.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 2913
    • Yang, N.C.1    Yang, D.H.2
  • 16
    • 0013543452 scopus 로고
    • Desiraju, G.R. Ed.; Elsevier: Amsterdam
    • For an early discussion, see Scheffer, J.R. In Organic Solid State Chemistry; Desiraju, G.R. Ed.; Elsevier: Amsterdam, 1987; pp. 1-45.
    • (1987) Organic Solid State Chemistry , pp. 1-45
    • Scheffer, J.R.1
  • 29
    • 0013552439 scopus 로고    scopus 로고
    • For other examples, see discussion by Wagner in reference 6b
    • For other examples, see discussion by Wagner in reference 6b, pp. 243-245.
  • 30
    • 0000222494 scopus 로고
    • (a) Kasha, M. Radiat. Res. 1960, Suppl. 2, 243;
    • (1960) Radiat. Res. , Issue.SUPPL. 2 , pp. 243
    • Kasha, M.1
  • 31
    • 0013544311 scopus 로고
    • (b) Zimmerman, H.E. Tetrahedron, 1963, 19, Suppl. 2, 393;
    • (1963) Tetrahedron , vol.19 , Issue.SUPPL. 2 , pp. 393
    • Zimmerman, H.E.1
  • 39
    • 18644371148 scopus 로고
    • and references cited therein
    • For example, it is well established that formaldehyde adopts a pyramidal geometry in its n,π* singlet and triplet excited states. See Moule, D.C.; Walsh, A.D. Chem. Rev. 1975, 75, 67 and references cited therein. Ab initio calculations by Sauers, R.R.; Edberg, L.A. J. Org. Chem. 1994, 59, 7061 on the triplet state geometries of aliphatic aldehydes and ketones support the picture of a partially (22-45°) pyramidalized carbonyl carbon.
    • (1975) Chem. Rev. , vol.75 , pp. 67
    • Moule, D.C.1    Walsh, A.D.2
  • 40
    • 33751157551 scopus 로고
    • For example, it is well established that formaldehyde adopts a pyramidal geometry in its n,π* singlet and triplet excited states. See Moule, D.C.; Walsh, A.D. Chem. Rev. 1975, 75, 67 and references cited therein. Ab initio calculations by Sauers, R.R.; Edberg, L.A. J. Org. Chem. 1994, 59, 7061 on the triplet state geometries of aliphatic aldehydes and ketones support the picture of a partially (22-45°) pyramidalized carbonyl carbon.
    • (1994) J. Org. Chem. , vol.59 , pp. 7061
    • Sauers, R.R.1    Edberg, L.A.2
  • 41
    • 0013513083 scopus 로고    scopus 로고
    • submitted for publication
    • In addition to an abstraction distance of 3.10 Å, the compound in question exhibited the following geometric parameters: ω = 56°, △ = 60° and θ = 117°. Cheung, E.; Netherton, M.R.; Scheffer, J.R.; Trotter, J. J. Am. Chem. Soc. submitted for publication.
    • J. Am. Chem. Soc.
    • Cheung, E.1    Netherton, M.R.2    Scheffer, J.R.3    Trotter, J.4
  • 52
    • 0000731679 scopus 로고
    • (b) For an earlier report on the same system that did not include any X-ray crystal structure data, see Aoyama, H.; Hasegawa, T.; Omote, Y. J. Am. Chem. Soc. 1979, 101, 5343;
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 5343
    • Aoyama, H.1    Hasegawa, T.2    Omote, Y.3
  • 56
    • 0000578420 scopus 로고
    • (b) Sakamoto, M.; Takahashi, M.; Fujita, T.; Nishio, T.; Iida, I.; Watanabe, S. J. Org. Chem. 1995, 60, 4682. In this case the C=O...H distance in the crystal is an impossibly long 4.45 Å, and abstraction is suggested to occur at defect lattice sites where bond rotations can occur.
    • (1995) J. Org. Chem. , vol.60 , pp. 4682
    • Sakamoto, M.1    Takahashi, M.2    Fujita, T.3    Nishio, T.4    Iida, I.5    Watanabe, S.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.