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1
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35548985408
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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
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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.
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2
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34249056927
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For more recent examples of C-C ring construction by intramolecular dipolar cycloaddition, see: a
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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.
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5
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6
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0007591091
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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
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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.
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7
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(b) Brinker, U. H.; Schrievers, T.; Xu, L. J. Am. Chem. Soc. 1990, 112, 8609.
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Ashby, E. C.; Park, B.; Patil, G.; S.; Gadru, K.; Gurumurthy, R. J. Org. Chem. 1993, 58, 424.
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(c) Ashby, E. C.; Park, B.; Patil, G.; S.; Gadru, K.; Gurumurthy, R. J. Org. Chem. 1993, 58, 424.
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9
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0034710469
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In each of these cases, ready tautomerization has commonly been observed
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(d) Jung, M. E.; Huang, A. Org. Lett. 2000, 2, 2659. In each of these cases, ready tautomerization has commonly been observed.
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Jung, M.E.1
Huang, A.2
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10
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0001482590
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For alternative methods for converting ketones to the corresponding diazo compounds, see
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(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.
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11
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0000628193
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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
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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.
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12
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85069134635
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The structure of 2a was established by X-ray analysis.
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The structure of 2a was established by X-ray analysis.
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13
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33947471020
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For an early report of the photolysis of cyclic diazenes to make cyclopropanes, see: a
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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.
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15
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0003131680
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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
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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.
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16
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22244459251
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For the reduction of hydrazine amides with SmI2, see: Shirakawa, S.; Lombardi, P. J.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 9974.
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For the reduction of hydrazine amides with SmI2, see: Shirakawa, S.; Lombardi, P. J.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 9974.
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0000293569
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For a representative cyclization of an ω-alkenyl diazo ketone, see
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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.
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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
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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.
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23
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85069139866
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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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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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