Generation and capture of iminyl radicals from ketoxime xanthates

Synlett

Volumn , Issue 12, 1999, Pages 1978-1980

  Gagosz, Fabien ^a   Zard, Samir Z ^a,b  

^a CNRS   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

5 exo cyclisation; Dihydropyrroles; Iminyl radicals

Indexed keywords

IMINE; PYRROLE DERIVATIVE; XANTHIC ACID DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS;

EID: 0032715089     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2971     Document Type: Article

References (15)

1. For a review of our work on iminyl radicals see: Zard, S. Z. Synlett 1996, 1148-1154.
2. See also: Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53,17543-17594.
3. (a) Boivin, J.; Fouquet, E. and Zard, S. Z. Tetrahedron 1994, 50,1745-1756.
4. (b) Boivin, J.; Fouquet, E.; Schiano A. -M. and Zard, S. Z. Tetrahedron 1994, 50, 1769-1776.
5. (c) Boivin, J.; Cailler-Dublanchet, A. -C.; Quiclet-Sire, B.; Schiano A. -M. and Zard, S. Z. Tetrahedron 1995, 51, 6517-6528.
6. (d) El Kaim, L. and Meyer, C. J. Org. Chem. 1996, 61, 1556-1557.
7. (e) Tadic Biadatti, M. -H. L.; Cailler-Dublanchet, A. -C.; Horner J. H.; Newcomb, M.; Quiclet-Sire, B. and Zard, S. Z. J. Org. Chem. 1997, 62, 559-563.
8. Uchiyama, K.; Hayashi, Y. and Narasaka, K. Tetrahedron 1999, 55, 8915-8930.
9. Lin, X.; Stien, D.; Weinreb, S. M. Organic Lett. 1999, 637. We thank Professor Wcinreb for kindly sending us a preprint of this publication.
10. Hudson, R. F.; Lawson, A. J. and Record, K. A. F. J. Chem. Soc. Perkin Trans. 2 1974, 869-873 and references cited therein.
11. (formula presented)
12. 3) δ 12.8, 19.7, 24.5, 24.8, 25.1, 39.4, 57.7, 80.3, 175.9, 189.2.
13. Irradiation of 2-allyl cyclopentanone oxime xanthate led to an 82% yield of the rearrangement product and some unidentified material.
14. Nitriles were produced as well as rearrangement products when aldoxime xanthates were irradiated. These results are in agreement with observations previously reported by Hudson and his co-workers: (a) Hudson, R. F. and Record, K. A. F. J. Chem. Soc. Chem. Comm. 1976, 539-540.
15. (b) Hudson, R. F. and Record, K. A. F. J. Chem. Soc. Perkin Trans. 2 1978, 1167-1171.