N-Hydroxypyridine-2-thione Carbamates as Aminyl and Aminium Radical Precursors: Cyclizations for Synthesis of the Pyrrolidine Nucleus

Journal of the American Chemical Society

Volumn 109, Issue 10, 1987, Pages 3163-3165

  Newcomb, Martin ^a   Deeb, Thomas M ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001414940     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00244a060     Document Type: Article

References (7)

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2. (a) Newcomb, M.; Park, S. U. ; Kaplan, J.; Marquardt, D. J. Tetrahedron Lett. 1985, 26, 5651–5654. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901–3924.
3. (a) Neale, R. S. Synthesis 1971, 1–15. Chow, Y. L.; Perry, R. A.; Menon, B. C.; Chen, S. C. Tetrahedron Lett. 1971, 1545–1549. Michejda, C. J.; Campbell, D. H.; Sieh, D. H., Koepke, S. R. In Organic Free Radicals; Pryor, W. A., Ed.; ACS Symposium Series 69, American Chemical Society: Washington, DC, 1978, pp 292–308. Bauer, R.; Wendt, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 202–203.
4. (a) Broka, C. A.; Eng, K. K. J. Org. Chem. 1986, 51, 5043–5045. Maeda, Y.; Ingold, K. U. J. Am. Chem. Soc. 1980,102, 328–331. Tokuda, M.; Yamada, Y., Takagi, T.; Suginome, H.; Furusaki, A. Tetrahedron Lett. 1985, 26, 6085–6088. Tokuda, M.; Yamada, Y.; Takagi, T.; Suginome, H. Tetrahedron 1987, 43, 281–296.
5. Fessenden, R. W.; Neta, D. J. Phys. Chem. 1972, 76, 2857–2859.
6. Surzur, J. M. ; Stella, L.Tetrahedron Lett. 1974 2191–2194.
7. compete with cyclization; cf.: Surzur, J. M. ; Stella, L.; Tordo, P. Bull. Soc, Chim. Fr. 1975. 1429–1430.