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Uncatalyzed reactions of this type are known, but they require heating at 200 ΰC for 12 h in a high-pressure autoclave (ca. 75% yield): Longley, R. I.; Emerson, W. S.; Blardinelli, A. J. In Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, 311. See especially note 6 therein. Clearly, catalysis by lanthanide complexes renders this chemistry considerably more practical.
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Uncatalyzed reactions of this type are known, but they require heating at 200 ΰC for 12 h in a high-pressure autoclave (ca. 75% yield): Longley, R. I.; Emerson, W. S.; Blardinelli, A. J. In Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, 311. See especially note 6 therein. Clearly, catalysis by lanthanide complexes renders this chemistry considerably more practical.
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33845455052
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Oxidation to p-quinones appears to be disfavored on steric grounds
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Oxidation to p-quinones appears to be disfavored on steric grounds: (a) Zimmer, H.; Lankin, D. C. Chem. Rev. 1971, 71, 229.
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For example, see: Padwa, A., Ed.; Wiley: New York, Chapter 12.
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For example, see: Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 2, Chapter 12.
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Padwa, A.1
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85022920766
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Reactions of this type are well precedented. For example, see
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Reactions of this type are well precedented. For example, see: (a) Pearson, W. H.; Lin, K.-C. Tetrahedron Lett. 1990, 31, 7531.
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For a discussion, see: Scriven, E. F. V., Ed.; Academic Press: Orlando, FL, Chapter 3. An alternative mechanistic interpretation is offered in ref 22.
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For a discussion, see: Smith, P. A. S. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic Press: Orlando, FL, 1984; Chapter 3. An alternative mechanistic interpretation is offered in ref 22.
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Heating is apparently necessary in order to favor hydrogen abstraction by the presumed triplet nitrene: See also ref 22.
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Heating is apparently necessary in order to favor hydrogen abstraction by the presumed triplet nitrene: Lindley, J. M.; McRobbie, I. M.; Meth-Cohn, O.; Suschitzsky, H. Tetrahedron Lett. 1976, 17, 4513. See also ref 22.
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