Novel intramolecular rearrangement of 3-bromo-3,3-difluoroalanine Schiff bases via radical ipso-substitution at the aromatic ring

Chemical Communications

Volumn , Issue 17, 1998, Pages 1845-1846

  Amii, Hideki ^a   Kondo, Susumu ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002758449     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803944e     Document Type: Article

References (12)

1. V. P. Kukhar' and V. A. Soloshonok, Fluorine-containing Amino Acids, Wiley, Chichester, UK, 1995.
2. A [3,3]-sigmatropic rearrangement route to β,β-difluoro-carbonyl compounds has been reported: see S. T. Patel, J. M. Percy and R. D. Wilkes, Tetrahedron, 1995, 51, 11 327.
3. T. Takagi, N. Okikawa, S. Johnoshita, M. Koyama, A. Ando and I. Kumadaki, Synlett, 1996, 82.
4. 2 in the presense of LDA has been reported: see P. Bay and J. P. Vevert, Tetrahedron Lett., 1978, 14, 1215.
5. Compound 4a was identified by comparison with an authentic sample synthesized by difluorination of ethyl benzoylacetate using DAST, see S. C. Sondej and J. A. Katzenellenbogen, J. Org. Chem., 1986, 51, 3508.
6. L. Benati, P. Spagnolo, A. Tundo and G. Zanardi, J. Chem. Soc., Chem. Commun., 1979, 141.
7. J. Grimshaw, R. Hamilton and J. Trocha-Grimshaw, J. Chem. Soc., Perkin Trans. 1, 1982, 229.
8. J. Aubé, X. Peng, Y. Wang and F. Takusagawa, J. Am. Chem. Soc., 1992, 114, 5466.
9. E. Lee, H. S. Whang and C. K. Chung, Tetrahedron Lett., 1995, 36, 913.
10. M. L. E. N. da Mata, W. B. Motherwell and F. Ujjainwalla, Tetrahedron Lett., 1997, 38, 137 and 141.
11. An equimolar amount of aromatic nitrile was isolated and identified by GC, NMR and IR analysis and comparison with authentic material.
12. M. J. O'Donnell and R. L. Polt, J. Org. Chem., 1982, 47, 2663.