A Modification of the Sheverdina-Kocheshkov Amination: The Use of Methoxyamine-Methyllithium as a Convenient Synthetic Equivalent for NH2+

Journal of Organic Chemistry

Volumn 47, Issue 14, 1982, Pages 2822-2823

  Beak, Peter ^a   Kokko, Bruce J ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000263951     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00135a040     Document Type: Letter

References (25)

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14. N,N-Dialkyl-O-mesitylenesulfonyl)hydroxylamine; Boche, G. Angew. Chem., Int. Ed. Engl. 1978, 17, 687.
15. O-,4-Dinitrophenyl)-hydroxylamine: Miller, M. J.; Loudon, G. M.; Radhakrishna, A. S. J. Org. Chem. 1979, 44, 4836.
16. Hydroxylamine-O-sulfonic acid: Wallace, R. G. Aldrichimica Acta 1980, 13, 3.
17. Yamada, S.; Oquri, T.; Shiori, T. J. Chem. Soc., Chem. Commun. 1972, 623.
18. O-Meistylenesulfonyl)-hydroxylamine: Tamura, Y.; Minamikowa, J.; Ikeda, M. Synthesis 1977, 1, 1.
19. Edwards, J. A.; Kluge, A. F.; Scopes, D. C. J. Org. Chem. 1977, 42, 376.
20. Primary and secondary amines with organocopper reagents and oxygen: Yamamoto, H.; Maruoka, K. J. Org. Chem. 1980, 45, 2739 and references cited therein.
21. 2 nitrogen, see the following. (a) Acetone oxime: Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1972, 1007.
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23. Azidomethyl phenyl sulfide: Trost, B. M.; Pearson, W. H. J. Am. Chem. Soc. 1981, 103, 2483.
24. Hassner, A.; Murger, P.; Belinha, B. A. Tetrahedron Lett. 1982, 699.
25. “Handbook of Chemistry of Physics”, 45th ed.; Weast, R. C., Ed.; The Chemical Rubber Co.: Cleveland, OH, 1964; p C-181.