Towards Improved Alkoxyl Radical Precursors - The Synthesis of N-Alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones

Synlett

Volumn 1997, Issue 7, 1997, Pages 848-850

  Hartung, Jens ^a   Schwarz, Michaela ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002640062     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5754     Document Type: Article

References (19)

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2. Johns, A.; Murphy, J.A. Tetrahedron Lett. 1988, 29 , 837.
3. Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095.
4. Barton, D.H.R.; Beaton, J.M.; Geller, L.E.; Pechet, M.M. J. Am. Chem. Soc. 1961, 83, 4076.
5. de Armas, P.; Concepción, J.I.; Francisco, C.G.; Hernández, R.; Salazar, J.A.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1989, 405; Ellwood, C.W.; Pattenden, G. Tetrahedron Lett. 1991, 32, 1591; Boto, A.; Hernandez, R.; Suárez, E. Tetrahedron Lett. 1994, 35, 2597.
6. de Armas, P.; Concepción, J.I.; Francisco, C.G.; Hernández, R.; Salazar, J.A.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1989, 405; Ellwood, C.W.; Pattenden, G. Tetrahedron Lett. 1991, 32, 1591; Boto, A.; Hernandez, R.; Suárez, E. Tetrahedron Lett. 1994, 35, 2597.
7. de Armas, P.; Concepción, J.I.; Francisco, C.G.; Hernández, R.; Salazar, J.A.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1989, 405; Ellwood, C.W.; Pattenden, G. Tetrahedron Lett. 1991, 32, 1591; Boto, A.; Hernandez, R.; Suárez, E. Tetrahedron Lett. 1994, 35, 2597.
8. Giese, B. Radicals in Organic Synthesis: The Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986.
9. Beckwith, A.L.J.; Hay, B.P. J. Org. Chem. 1989, 54, 4330; Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230.
10. Beckwith, A.L.J.; Hay, B.P. J. Org. Chem. 1989, 54, 4330; Beckwith, A.L.J.; Hay, B.P. J. Am. Chem. Soc. 1989, 111, 230.
11. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413.
12. Hartung, J.; Hiller, M.; Schmidt, P. Chem. Eur. J. 1996, 2, 1014.
13. Barton, D.H.R.; Crich, D.; Kretzschmar, G. J. Chem. Soc., Perkin Trans. 1 1986, 39.
14. 2 (243.7): calcd. C 44.35, H 2.48, N 5.75, S 26.31, found C 44.35, H 2.47, N 5.74, S 26.39.
15. 2 (388.0): calcd. C 61.92, H 4.68, N 3.61, S 16.53, found C 61.74, H 4.77, N 3.75, S 16.39.
16. 3, 25°C, 100 MHz): δ = 37.4, 40.1, 46.1, 113.2, 117.3, 127.1, 127.7. 128.5, 128.8, 129.3, 135.4, 135.9, 142.1, 146.0.
17. 2 (285.8): calcd. C 46.23, H 2.82, N 4.90, S 22.44, found C 46.52, H 2.90, N 4.80, S 22.44.
18. Hartung, J.; Hiller, M.; Schwarz, M.; Svoboda, I.; Fuess, H. Liebigs Ann. 1996, 2091.
19. 30 as internal standard (averaged values of 2 independent runs; experimental error exo:endo ratios vary within 0.