Regioselective nucleophilic substitutions of fluorobenzene derivatives

Tetrahedron Letters

Volumn 37, Issue 36, 1996, Pages 6439-6442

  Wells, Kenneth M ^a   Shi, Yao Jun ^a   Lynch, Joseph E ^a   Humphrey, Guy R ^a   Volante, R P ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030565552     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01425-6     Document Type: Article

References (9)

1. Williams, P.D.; Clineschmidt, B.V.; Erb, J.M.; Freidinger, R.M.; Guidotti, M.T.; Lis, E.V.; Pawluczyk, J.M.; Pettibone, D.J.; Reiss, D.R.; Veber, D.F.; Woyden, C.J. J. Med. Chem. 1995, 38, 4634-4636.
2. N-Boc-4-piperidinol was prepared from 4-piperidinol (Aldrich) and di-t-butyl-dicarbonate.
3. a) P. Tarrant (ed.), "Fluorine Chemistry Review," Vol. 7, Marcel Dekker, New York, 1974, pp. 1-114
4. b) Brown, F.C.; Bradsher, C.K.; Reiss, J.R.; Tetenbaum, M. J. Org. Chem. 1961, 26, 4707-4708.
5. c) Slade, J; Stanton, J.L.; Ben-David, D.; Mazzenga, G.G. J. Med. Chem. 1985, 25, 1517-1521.
6. A limited report of the selectivity of displacements of o,p-difluorophenyl ketone systems has appeared: Sasajima, K.; Ona, K.; Katsube, J.; Yamamoto, H. Chem. Pharm. Bull. 1978, 26, 2502-2507.
7. McCloskey, A.L.; Forken, G.S.; Kluiber, R.W.; Johnson, W.S. Org. Syn. Coll. Vol. IV, 1963, 261.
8. C-F= 240 Hz), 120.2 (d, JC-F = 22.8 Hz), 115.7, 101.0, 93.1, 79.7, 74.8, 56.7, 30.4, 28.4, 26.9.
9. Dankwardt, S.M.; Newman, S.R.; Krstenansky, J.L. Tetrahedron Lett ., 36, 1995, 4923.