A facile protocol for the convenient preparation of amino-substituted α-bromo- and α,α-dibromo arylmethylketones

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 4987-4990

  Diwu, Zhenjun ^a   Beachdel, Christopher ^a   Klaubert, Dieter H ^a  

^a MOLECULAR PROBES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DEBROMINATION; SYNTHESIS;

EID: 0032499980     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00975-7     Document Type: Article

References (11)

1. 1. Kimpe, N. D.; Verhe, R. The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines. In The Chemistry of Functional Groups; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: Chichester, 1988; pp.1-119.
2. 2. Taylor, R. Electrophilic Aromatic Substitution; John Wiley & Sons: Chichester, 1990.
3. 3. Diwu, Z.; Lu, Y.; Zhang, C.; Klaubert, D. H.; Haugland, R. P. Photochem. Photobiol. 1997, 66, 424-431.
4. 4. Fedyunyaeva, A.; Shershukov, V. M. Khimiya Geterotsiklicheskikh Soedinenii 1993, 234-237.
5. 5. King, L. C.; Ostrum, G. K. J. Org. Chem. 1964, 29, 3459-3461.
6. 6. Pasaribu, S. J.; Williams, L. R. Aust. J. Chem. 1973, 26, 1327-1331.
7. 7. Calo, V.; Lopez, L.; Pesce, G.; Todesco, P. E. Tetrahedron 1973, 29, 1625-1628.
8. 8. Djerassi, C.; Lenk, C. T. J. Am. Chem. Soc. 1953, 75, 3493-3495.
9. 9. Reuss, R. H.; Hassner, A. H. J. Org. Chem. 1974, 39, 1785-1787.
10. 10. Blanco, L.; Amice, P.; Conia, J. M. Synthesis 1976, 194-196.
11. 3) spectra for compounds III and IV. Compound IIIb: 7.86 (2H, dd, J = 10 Hz); 6.90 (2H, dd, J = 10 Hz); 4.46 (2H, s); 3.40 (4H, m) and 1.67 ppm (6H, m). Compound IIIc: 7.90 (2H, dd, J = 10 Hz); 6.83 (2H, dd, J = 10 Hz); 4.47 (1H, s); 3.86 (4H, m) and 3.37 ppm (4H, m). Compound IIId: 8.38 (1H, m); 7.92 (1H, m); 7.82 (1H, m); 7.63 (1H, m); 7.17 (1H, m); 6.88 (1H, m); 4.53 (2H, s) and 3.15 ppm (4H, m). Compound IVb: 7.95 (2H, dd, J = 10 Hz); 6.82 (2H, dd, J = 10 Hz); 6.68 (1H, s); 3.44 (4H, m) and 1.68 ppm (6H, m). Compound IVc: 8.00 (2H, dd, J = 10 Hz); 6.89 (2H, dd, J = 10 Hz); 6.68 (1H, s); 3.88 (4H, m) and 3.38 ppm (4H, m). Compound IVd: 8.46 (1H, m); 7.96 (1H, m); 7.84 (1H, m); 7.66 (1H, m); 7.23 (1H, m); 6.95 (1H, m); 6.92 (1H, s) and 3.16 ppm (4H, m).