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Volumn 55, Issue 12, 1999, Pages 3585-3594

H(ax) vs. H(eq) migrations in tetrahydropyranylidenes generated Bamford- Stevens reactions. Temperature dependence and non-stereoselective activation by ring oxygen

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; KETONE; OXYGEN; TETRAHYDROPYRAN DERIVATIVE; TETRAHYDROPYRANYLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033583262     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01165-X     Document Type: Article
Times cited : (6)

References (44)
  • 1
    • 0002216732 scopus 로고
    • For a discussion and leading references see: Nickon, A. Acc. Chem. Res. 1993, 26, 84-89.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 84-89
    • Nickon, A.1
  • 4
    • 0013578456 scopus 로고    scopus 로고
    • note
    • (c) Footnotes 2 and 3 in ref. 1.
  • 16
    • 0013607838 scopus 로고
    • Gould, K.A. Ph.D. Thesis, The Ohio State University
    • Shechter, H. Personal Communication. See: Gould, K.A. Ph.D. Thesis, The Ohio State University, 1975; Diss. Abstr. Int. 1975, 36, 2806-B.
    • (1975)
    • Shechter, H.1
  • 17
    • 0013581783 scopus 로고
    • Shechter, H. Personal Communication. See: Gould, K.A. Ph.D. Thesis, The Ohio State University, 1975; Diss. Abstr. Int. 1975, 36, 2806-B.
    • (1975) Diss. Abstr. Int. , vol.36 , pp. 2806-B
  • 18
    • 0013610339 scopus 로고    scopus 로고
    • note
    • We show here only Z-alkene proportions (not E) for later comparison with cyclic carbenes where the derived cyclohexenes necessarily must have Z stereochemistry.
  • 22
    • 0027197861 scopus 로고
    • (b) Stern, A.G.; Ilao, M.C.; Nickon, A. Tetrahedron 1993, 49, 8107-8118. The reported photochemical value (1.17 at 25 °C) becomes 1.40 alter adjustment for isotope effects as described in ref. 10b, footnote 32.
    • (1993) Tetrahedron , vol.49 , pp. 8107-8118
    • Stern, A.G.1    Ilao, M.C.2    Nickon, A.3
  • 24
    • 0013610340 scopus 로고    scopus 로고
    • note
    • 3). The NMR of the alkene mixture from B-S on 6 (conducted thermally at 170 °C, 120 °C, and 95 °C, and photically at -70 °C) lacked those vinyl peaks. For details see: Kim, K. Ph.D. Dissertation, Johns Hopkins University, 1986.
  • 25
    • 0013580587 scopus 로고    scopus 로고
    • note
    • (b) Interestingly, had ring oxygen migration taken place, the D-labeled substrates 14 could have revealed whether that rearrangement proceeded from a chair-like or boat-like precursor, because each of these cyclohexyl conformations destines the deuterium to a different stereochemistry in the methylene unit of the ring-contracted product.
  • 26
    • 0001412364 scopus 로고
    • For theories of anomeric effects and leading references see: Salzner, U.; Schleyer, P.v.R. J. Org. Chem. 1994, 59, 2138-2155.
    • (1994) J. Org. Chem. , vol.59 , pp. 2138-2155
    • Salzner, U.1    Schleyer, P.V.R.2
  • 34
    • 0004050551 scopus 로고
    • Academic: New York
    • For reviews of the Bamford-Stevens reaction see: (a) Kirmse, W. Carbene Chemistry, 2nd Ed.; Academic: New York, 1971.
    • (1971) Carbene Chemistry, 2nd Ed.
    • Kirmse, W.1
  • 35
  • 38
    • 0030948966 scopus 로고    scopus 로고
    • and also ref. 5
    • In photolysis of diazirines, oxadiazolines, and perhaps also diazohydrocarbons, alkene products can also arise in part directly from excited states of carbene precursors. For leading references see: Pezacki, J.P.; Pole, D.L.; Warkentin, J.; Chen, T.; Ford, F.; Toscano, J.P.; Ford, J.; Platz, M.S. J. Am. Chem. Soc. 1997, 119, 3191-3193 and also ref. 5.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 3191-3193
    • Pezacki, J.P.1    Pole, D.L.2    Warkentin, J.3    Chen, T.4    Ford, F.5    Toscano, J.P.6    Ford, J.7    Platz, M.S.8
  • 41
    • 0002312550 scopus 로고
    • Brinker, U.H., Ed.; JAI Press, Greenwich, CT
    • (b) For discussions of isotope effects and possible tunneling see: Jackson, J.E.; Platz, M.S. In Advances in Carbene Chemistry, Brinker, U.H., Ed.; JAI Press, Greenwich, CT, Vol. 1, 1994, pp 89-160, and Liu, M.T.H. Acc. Chem. Res. 1994, 27, 287-294.
    • (1994) Advances in Carbene Chemistry , vol.1 , pp. 89-160
    • Jackson, J.E.1    Platz, M.S.2
  • 42
    • 0002843719 scopus 로고
    • (b) For discussions of isotope effects and possible tunneling see: Jackson, J.E.; Platz, M.S. In Advances in Carbene Chemistry, Brinker, U.H., Ed.; JAI Press, Greenwich, CT, Vol. 1, 1994, pp 89-160, and Liu, M.T.H. Acc. Chem. Res. 1994, 27, 287-294.
    • (1994) Acc. Chem. Res. , vol.27 , pp. 287-294
    • Liu, M.T.H.1


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