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Volumn 73, Issue 23, 2008, Pages 9479-9481

Convenient access to bicyclic and tricyclic diazenes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CHEMICAL REACTIONS; KETONES; PROPANE; TOLUENE;

EID: 57449084348     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8017704     Document Type: Article
Times cited : (57)

References (23)
  • 1
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    • For a recent review of the use of intramolecular dipolar cycloaddition in target-directed organic synthesis, see: Nair, V, Suja, T. D. Tetrahedron 2007, 63, 12247. It should be noted that the intramolecular cycloaddition of an ω-alkenyl diazo alkane to form the cyclic diazene is not mentioned in this thorough review
    • For a recent review of the use of intramolecular dipolar cycloaddition in target-directed organic synthesis, see: Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247. It should be noted that the intramolecular cycloaddition of an ω-alkenyl diazo alkane to form the cyclic diazene is not mentioned in this thorough review.
  • 2
    • 34249056927 scopus 로고    scopus 로고
    • For more recent examples of C-C ring construction by intramolecular dipolar cycloaddition, see: a
    • For more recent examples of C-C ring construction by intramolecular dipolar cycloaddition, see: (a) Huang, X.; Zhang, L. J. Am. Chem. Soc. 2007, 129, 6398.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 6398
    • Huang, X.1    Zhang, L.2
  • 6
    • 0007591091 scopus 로고    scopus 로고
    • There have been isolated reports over the years of the cyclization of simple alicyclic ω-alkenyl ketones and aldehydes to the cyclic diazenes. For the most detailed account, see: (a) Padwa, A, Ku, H. J. Org. Chem. 1980, 45, 3756
    • There have been isolated reports over the years of the cyclization of simple alicyclic ω-alkenyl ketones and aldehydes to the cyclic diazenes. For the most detailed account, see: (a) Padwa, A.; Ku, H. J. Org. Chem. 1980, 45, 3756.
  • 8
    • 0012103407 scopus 로고    scopus 로고
    • Ashby, E. C.; Park, B.; Patil, G.; S.; Gadru, K.; Gurumurthy, R. J. Org. Chem. 1993, 58, 424.
    • (c) Ashby, E. C.; Park, B.; Patil, G.; S.; Gadru, K.; Gurumurthy, R. J. Org. Chem. 1993, 58, 424.
  • 9
    • 0034710469 scopus 로고    scopus 로고
    • In each of these cases, ready tautomerization has commonly been observed
    • (d) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659. In each of these cases, ready tautomerization has commonly been observed.
    • (2000) Org. Lett , vol.2 , pp. 2659
    • Jung, M.E.1    Huang, A.2
  • 10
    • 0001482590 scopus 로고
    • For alternative methods for converting ketones to the corresponding diazo compounds, see
    • (e) For alternative methods for converting ketones to the corresponding diazo compounds, see: Miller, P. C.; Gaspar, P. P. J. Org. Chem. 1991, 56, 5101.
    • (1991) J. Org. Chem , vol.56 , pp. 5101
    • Miller, P.C.1    Gaspar, P.P.2
  • 11
    • 0000628193 scopus 로고    scopus 로고
    • For the single instance of the use of intramolecular addition of a diazo alkane to an alkene in natural product synthesis, see: Schultz, A. G, Puig, S. J. Org. Chem. 1985, 50, 915. Note that in this case, conversion of the aldehyde to the intermediate diazo alkane by reaction with an N-aminoaziridine also led to the nitrile as a major byproduct
    • For the single instance of the use of intramolecular addition of a diazo alkane to an alkene in natural product synthesis, see: Schultz, A. G.; Puig, S. J. Org. Chem. 1985, 50, 915. Note that in this case, conversion of the aldehyde to the intermediate diazo alkane by reaction with an N-aminoaziridine also led to the nitrile as a major byproduct.
  • 12
    • 85069134635 scopus 로고    scopus 로고
    • The structure of 2a was established by X-ray analysis.
    • The structure of 2a was established by X-ray analysis.
  • 13
    • 33947471020 scopus 로고
    • For an early report of the photolysis of cyclic diazenes to make cyclopropanes, see: a
    • For an early report of the photolysis of cyclic diazenes to make cyclopropanes, see: (a) Rinehart, K. L., Jr.; Van Auken, T. L. J. Am. Chem. Soc. 1960, 82, 5251.
    • (1960) J. Am. Chem. Soc , vol.82 , pp. 5251
    • Rinehart Jr., K.L.1    Van Auken, T.L.2
  • 15
    • 0003131680 scopus 로고    scopus 로고
    • For leading references to efforts toward cyclopropane construction by the conversion of ketones into carbene equivalents, see: Motherwell, W. B. J. Organomet. Chem. 2001, 624, 41
    • For leading references to efforts toward cyclopropane construction by the conversion of ketones into carbene equivalents, see: Motherwell, W. B. J. Organomet. Chem. 2001, 624, 41.
  • 16
    • 22244459251 scopus 로고    scopus 로고
    • For the reduction of hydrazine amides with SmI2, see: Shirakawa, S.; Lombardi, P. J.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 9974.
    • For the reduction of hydrazine amides with SmI2, see: Shirakawa, S.; Lombardi, P. J.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 9974.
  • 18
    • 0000293569 scopus 로고
    • For a representative cyclization of an ω-alkenyl diazo ketone, see
    • For a representative cyclization of an ω-alkenyl diazo ketone, see: Taber, D. F.; Saleh, S. A.; Korsmeyer, R. W. J. Org. Chem. 1980, 45, 4699.
    • (1980) J. Org. Chem , vol.45 , pp. 4699
    • Taber, D.F.1    Saleh, S.A.2    Korsmeyer, R.W.3
  • 20
    • 0027432752 scopus 로고    scopus 로고
    • For a complementary carbacyclization of ω-alkenyl ketone tosylhydrazones via the derived alkyl radicals, see: (a) Taber, D. F, Wang, Y, Stachel, S. J. Tetrahedron Lett. 1993, 34, 6209
    • For a complementary carbacyclization of ω-alkenyl ketone tosylhydrazones via the derived alkyl radicals, see: (a) Taber, D. F.; Wang, Y.; Stachel, S. J. Tetrahedron Lett. 1993, 34, 6209.
  • 23
    • 85069139866 scopus 로고    scopus 로고
    • 13C multiplicities were determined with the aid of a JVERT pulse sequence, differentiating the signals for methyl and methine carbons as d and for methylene and quaternary carbons as u.
    • 13C multiplicities were determined with the aid of a JVERT pulse sequence, differentiating the signals for methyl and methine carbons as "d" and for methylene and quaternary carbons as "u".


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