Regioselective functionalization. 6. Migratory preferences in hydroxylamine-O-sulfonic acid and Schmidt rearrangements of 7-substituted norcamphors

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5574-5580

  Krow, Grant R ^a   Cheung, Osbert H ^a   Hu, Zilun ^a   Lee, Yoon B ^b  

^a Temple University   (United States)

^b Soonchunhyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008086132     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960604e     Document Type: Article

References (49)

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2. For previous papers in this series, see: (a) Krow, G. R.; Szczepanski, S. J. Org. Chem. 1982, 47, 1153. (b) Krow, G. R.; Lee, Y. B. Trends Org. Chem. 1992, 3, 289.
3. For a review of nitrogen insertions in bridged bicyclic ketones, see: Krow, G. R. Tetrahedron 1981, 37, 1283.
4. For an early review of the Schmidt reaction, see: (a) Smith, P. A. S. In Molecular Rearrangements; de Mayo, P., Ed.; Wiley-Interscience: New York, 1963; Vol. 1, pp 507-526. (b) For a recent discussion of the mechanism of the Schmidt reaction, see: Sprecher, M.; Kost, D. J. Am..Chem. Soc. 1994, 116, 1016. (c) Shioiri, T. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6, pp 798, 820. (d) An efficient asymmetric Schmidt reaction of symmetrical ketones utilizing chiral 1,2-azidohydrins has recently been described: Gracias, V.; Milligan, G. L.; Aube, J. J. Am. Chem. Soc. 1995, 117, 8047.
5. For an early review of the Schmidt reaction, see: (a) Smith, P. A. S. In Molecular Rearrangements; de Mayo, P., Ed.; Wiley-Interscience: New York, 1963; Vol. 1, pp 507-526. (b) For a recent discussion of the mechanism of the Schmidt reaction, see: Sprecher, M.; Kost, D. J. Am..Chem. Soc. 1994, 116, 1016. (c) Shioiri, T. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6, pp 798, 820. (d) An efficient asymmetric Schmidt reaction of symmetrical ketones utilizing chiral 1,2-azidohydrins has recently been described: Gracias, V.; Milligan, G. L.; Aube, J. J. Am. Chem. Soc. 1995, 117, 8047.
6. For an early review of the Schmidt reaction, see: (a) Smith, P. A. S. In Molecular Rearrangements; de Mayo, P., Ed.; Wiley-Interscience: New York, 1963; Vol. 1, pp 507-526. (b) For a recent discussion of the mechanism of the Schmidt reaction, see: Sprecher, M.; Kost, D. J. Am..Chem. Soc. 1994, 116, 1016. (c) Shioiri, T. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6, pp 798, 820. (d) An efficient asymmetric Schmidt reaction of symmetrical ketones utilizing chiral 1,2-azidohydrins has recently been described: Gracias, V.; Milligan, G. L.; Aube, J. J. Am. Chem. Soc. 1995, 117, 8047.
7. For an early review of the Schmidt reaction, see: (a) Smith, P. A. S. In Molecular Rearrangements; de Mayo, P., Ed.; Wiley-Interscience: New York, 1963; Vol. 1, pp 507-526. (b) For a recent discussion of the mechanism of the Schmidt reaction, see: Sprecher, M.; Kost, D. J. Am..Chem. Soc. 1994, 116, 1016. (c) Shioiri, T. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6, pp 798, 820. (d) An efficient asymmetric Schmidt reaction of symmetrical ketones utilizing chiral 1,2-azidohydrins has recently been described: Gracias, V.; Milligan, G. L.; Aube, J. J. Am. Chem. Soc. 1995, 117, 8047.
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22. A number of carbon ring expansions in norcamphor systems, in which migration occurs toward an endo-oriented methylene group, show an increased tendency toward methylene migration relative to their exo-substituted counterparts. There is almost all methylene migration in the solvolysis of endo-2-norbornylcarbinyl brosylates and in the deamination of endo-2-norbornylcarbinylamine; the exo isomers give predominant, but less, methylene migration; Krow, G. R. Tetrahedron 1987, 43, 3, especially footnote 18.
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27. 5d In a reinterpretation consistent with the present findings, the results also can be explained by low stereoselectivity in a rate-determining dehydration step to form syn- and anti-iminodiazonium ions analogous to 42. The syn-iminodiazonium ion rearranges to give lactam 12, while the anti-isomer gives cleavage products.
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39. (a) March, J. Advanced Organic Chemistry, 4th ed.; J. Wiley and Sons: NY, 1992; p 312. Iodine and bromine are more effective as neighboring groups than chlorine, which provides anchimeric assistance only when there is a need for it. Anchimeric assistance might be aided in the present instance by poor solvation at C-1 during C-C bond breaking.
40. (b) Duddeck, H.; Brosch, D.; Koppetsch, G. Tetrahedron 1985, 41, 3753. In methanesulfonic acid-catalyzed Schmidt reactions of 4-substituted adamantanones (syn/anti 4-OMes, I, Br, Cl, and CN) the anti-Cl, Br, and I compounds behaved unusually. Alkene carbonitriles were isolated from cleavage at the bridgehead adjacent to an anti-bromo or anti-chloro substituent, but not a syn-bromo or syn-chloro or other substituent. Only anti-4-iodoadamantanone gave the regioisomer derived by migration of the C-1 bridgehead distal to the substituent as the major or only lactam isolated. It is suggested that for the adamantanone system, an anti-iodo substituent facilitates bridgehead cleavage rather than migration; unfortunately, major amounts of cleavage products from reactions of this substrate have not been identified. For the other 4-substituted adamantanone substrates, the inductive effect of the substituent facilitates the isolation of lactam product (14-44% lactam) when compared to the parent adamantanone (11% lactam).
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