The acidifying effects of chlorine and bromine: Little difference

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1559-1562

  Mongin, Florence ^a   Schlosser, Manfred ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BENZOIC ACID DERIVATIVE; BROMINE; CHLORINE;

ACIDIFICATION; ARTICLE; CARBOXYLATION; DRUG SYNTHESIS; HALOGENATION; PROTON TRANSPORT;

EID: 0031550808     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00131-7     Document Type: Article

References (15)

1. 1. Schlosser, M.; in Organometallics in Synthesis : A Manual (ed. Schlosser, M.), Wiley Chichester, 1994, pp. 100-101.
2. 2. Aue, D.H.; Webb, H.M.; Davidson, W.R.; Toure, P. Hopkins, H.P.; Moulik, S.P.; Jahagirdar, D.V.; J. Am. Chem. Soc. 1991, 113, 1770.
3. 3. Perrin, D.D.; Dissociation Constants of Organic Bases in Aqueous Solution, Butterworth, London, 1965.
4. 4. Moyroud, J.; Guesnet, J.-L.; Bennetau, B.; Mortier, J.; Tetrahedron Lett. 1995, 36, 881-884; Moyroud, J.; Guesnet, J.-L.; Bennetau, B.; Mortier, J.; Bull. Soc. Chim. Fr. 1996, 133, 133-141.
5. 4. Moyroud, J.; Guesnet, J.-L.; Bennetau, B.; Mortier, J.; Tetrahedron Lett. 1995, 36, 881-884; Moyroud, J.; Guesnet, J.-L.; Bennetau, B.; Mortier, J.; Bull. Soc. Chim. Fr. 1996, 133, 133-141.
6. 5 . Reviews : Bunnett, J.F.; Acc. Chem. Res. 1972, 5, 139-147; Quéguiner, G.; Marsais, F.; Snieckus, V.; Epstain, J.; Adv. Heterocycl. Chem. 1991, 52, 187-304, spec. 199-202; Fröhlich, J.; Progress Heterocycl. Chem. 1994, 6, 1-35.
7. 5 . Reviews : Bunnett, J.F.; Acc. Chem. Res. 1972, 5, 139-147; Quéguiner, G.; Marsais, F.; Snieckus, V.; Epstain, J.; Adv. Heterocycl. Chem. 1991, 52, 187-304, spec. 199-202; Fröhlich, J.; Progress Heterocycl. Chem. 1994, 6, 1-35.
8. 5 . Reviews : Bunnett, J.F.; Acc. Chem. Res. 1972, 5, 139-147; Quéguiner, G.; Marsais, F.; Snieckus, V.; Epstain, J.; Adv. Heterocycl. Chem. 1991, 52, 187-304, spec. 199-202; Fröhlich, J.; Progress Heterocycl. Chem. 1994, 6, 1-35.
9. 6. For a close analogy, see : Mongin, F.; Desponds, O.; Schlosser, M.; Tetrahedron Lett. 1996, 37, 2767-2770.
10. 7. Liedholm, B.; Acta Chem. Scand., Ser. B 1984, B 38, 713-715.
11. 8. Doyle, E.P.; Nayler, J.H.C.; Waddington, H.R.J.; Hanson, J.C.; Thomas, G.R.; J. Chem. Soc. 1963, 497-506.
12. 9. Acheson, R.M.; Robinson, M.J.T.; J. Chem. Soc. 1953, 232-238.
13. 10. Vingiello, F.A.; Buese, G.J.; Newallis, P.E.; J. Org. Chem. 1958, 23, 1139-1142.
14. 11. To prepare 1,3-dibromo-5-chlorobenzene, 1,3,5-tribroinobenzene was consecutively treated with butyllithium [see : Chen, L.S.; Chen, G.J.; Tamborski, C.; J. Organomet. Chem. 1981, 215, 281-291] and hexachloroethane.
15. 12. Asinger, F.; J. prakt. Chem. 1935, 142, 291-300.