Cyclisation of unsaturated N-chloroamines under acidic conditions: A polar reaction via chloronium ions

Synlett

Volumn , Issue 6, 2004, Pages 1110-1112

  Noack, Michael ^a   Kalsow, Stefanie ^a   Göttlich, Richard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Addition reactions; Aminations; Cyclisation; Heterocycles

Indexed keywords

AMINE; CHLORINE DERIVATIVE; FREE RADICAL;

ACIDITY; ARTICLE; CYCLIZATION; RADICAL REACTION; REACTION ANALYSIS;

EID: 3142692420     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822907     Document Type: Article

References (22)

1. For reviews see: (a) Minisci, F. Synthesis 1973, 1. (b) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337. (c) Stella, L. In Radicals in Organic Synthesis, Vol. 2; Wiley-VCH: Weinheim, 2001, 407.
2. For reviews see: (a) Minisci, F. Synthesis 1973, 1. (b) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337. (c) Stella, L. In Radicals in Organic Synthesis, Vol. 2; Wiley-VCH: Weinheim, 2001, 407.
3. For reviews see: (a) Minisci, F. Synthesis 1973, 1. (b) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337. (c) Stella, L. In Radicals in Organic Synthesis, Vol. 2; Wiley-VCH: Weinheim, 2001, 407.
4. (a) Hemmerling, M.; Sjöholm, Å.; Somfai, P. Tetrahedron: Asymmetry 1999, 10, 4091.
5. (b) Sjöholm, Å.; Hemmerling, M.; Pradeille, N.; Somfai, P. J. Chem. Soc., Perkin Trans. 1 2001, 891.
6. (a) Stella, L.; Raynier, B.; Surzur, J. M. Tetrahedron 1981, 37, 2843.
7. (b) Borch, R. F.; Evans, A. J.; Wade, J. J. J. Am. Chem. Soc. 1975, 97, 6282.
8. Roush, W. R. J. Am. Chem. Soc. 1980, 102, 1390.
9. (a) Newcomb, M.; Deeb, T. M.; Marquardt, D. J. Tetrahedron 1990, 46, 2317.
10. (b) Horner, J. H.; Martinez, F. N.; Musa, O. M.; Newcomb, M.; Shahin, H. E. J. Am. Chem. Soc. 1995, 117, 11124.
11. (a) Göttlich, R.; Noack, M. Tetrahedron Lett. 2001, 7771.
12. (b) Noack, M.; Göttlich, R. Eur. J. Org. Chem. 2002, 3171.
13. We have performed the reaction in deuterated acetic acid and detected the intermediate by NMR.
14. This rearrangement is known: (a) Fusaon, R. C.; Zirkle, C. L. J. Am. Chem. Soc. 1948, 70, 2760. (b) Hammer, C. F.; Heller, S. R.; Craig, J. H. Tetrahedron 1972, 28, 239.
15. This rearrangement is known: (a) Fusaon, R. C.; Zirkle, C. L. J. Am. Chem. Soc. 1948, 70, 2760. (b) Hammer, C. F.; Heller, S. R.; Craig, J. H. Tetrahedron 1972, 28, 239.
16. In the first reports by Minisci a polar mechanism was always considered as an alternative reaction pathway: (a) Minisci, F.; Galli, R.; Cecere, M. Chim. Ind. (Milan, Italy) 1966, 48, 347. (b) Neale, R. S. J. Org. Chem. 1967, 32, 3263. (c) Surzur, J.-M.; Stella, L.; Tordo, P. Bull. Soc. Chim. Fr. 1970, 115. (d) For other experiments using Lewis acids see: Heumann, A.; Furstoss, R.; Waegell, B. Tetrahedron Lett. 1972, 993.
17. In the first reports by Minisci a polar mechanism was always considered as an alternative reaction pathway: (a) Minisci, F.; Galli, R.; Cecere, M. Chim. Ind. (Milan, Italy) 1966, 48, 347. (b) Neale, R. S. J. Org. Chem. 1967, 32, 3263. (c) Surzur, J.-M.; Stella, L.; Tordo, P. Bull. Soc. Chim. Fr. 1970, 115. (d) For other experiments using Lewis acids see: Heumann, A.; Furstoss, R.; Waegell, B. Tetrahedron Lett. 1972, 993.
18. In the first reports by Minisci a polar mechanism was always considered as an alternative reaction pathway: (a) Minisci, F.; Galli, R.; Cecere, M. Chim. Ind. (Milan, Italy) 1966, 48, 347. (b) Neale, R. S. J. Org. Chem. 1967, 32, 3263. (c) Surzur, J.-M.; Stella, L.; Tordo, P. Bull. Soc. Chim. Fr. 1970, 115. (d) For other experiments using Lewis acids see: Heumann, A.; Furstoss, R.; Waegell, B. Tetrahedron Lett. 1972, 993.
19. In the first reports by Minisci a polar mechanism was always considered as an alternative reaction pathway: (a) Minisci, F.; Galli, R.; Cecere, M. Chim. Ind. (Milan, Italy) 1966, 48, 347. (b) Neale, R. S. J. Org. Chem. 1967, 32, 3263. (c) Surzur, J.-M.; Stella, L.; Tordo, P. Bull. Soc. Chim. Fr. 1970, 115. (d) For other experiments using Lewis acids see: Heumann, A.; Furstoss, R.; Waegell, B. Tetrahedron Lett. 1972, 993.
20. 22NCl, calcd: 203.14358; found: 203.14426.
21. In the proposed radical-type cyclisations of chloroamines by Somfai, borontrifluoride etherate was found to be the superior Lewis acid too (see ref. 3).
22. For an overview see: Jung, M. F. Synlett 1999, 843.