A flexible, convergent approach to piperidines, pyridines, azepines, and related derivatives

Tetrahedron Letters

Volumn 40, Issue 19, 1999, Pages 3701-3704

  Boivin, Jean ^a   Pothier, Julien ^a   Zard, Samir Z ^a,b  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033532243     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00592-4     Document Type: Article

References (22)

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2. 2. Jones, G. in Comprehensive Heterocyclic Chemistry II. Katritzky, A.R.; Rees, C.W.; Scriven, E.F.V., Eds; Elsevier Science, Oxford, 1997, 5, 167-244. For a review on 2,6-Disubstituted piperidines see: Balia, V.; Jeyaraman, R.;Chandrasekaran, L. Chem. Rev. 1983, 83, 379-423. For a recent example see: Laschat, S.; Frölich, R.; Wibbeling, B. J.Org. Chem., 1996, 61, 2829-2838.
3. 2. Jones, G. in Comprehensive Heterocyclic Chemistry II. Katritzky, A.R.; Rees, C.W.; Scriven, E.F.V., Eds; ElsevierScience, Oxford, 1997, 5, 167-244. For a review on 2,6-Disubstituted piperidines see: Balia, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379-423. For a recent example see: Laschat, S.; Frölich, R.; Wibbeling, B. J.Org. Chem., 1996, 61, 2829-2838.
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6. 4. In a typical experiment, a mixture of the xanthate and 2 or more equivalents of the olefin in cyclohexane were degassed under argon for 30 min at reflux, then lauroyl peroxide was added in small portions (2% mol) every two hours. The reaction is monitored by thin layer chromatography for completion. The resulting adduct was purified, after evaporation of the solvent, by silica gel chromatography.
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21. 3): δ 145.9; 128.5; 127.2; 127.0; 64.1; 62.9; 35.0; 32.0; 25.6; 17.7; 3.0; 2.4. Calculated %C 83.53 %H 9.51. Found %C 83.62 %H 9.39. Three compounds are already known: : 11a: Sashida, H.; Tsuchiya, T. Chem. Pharm. Bull. 1984, 32, 4117-4123; 22: Gutierrez, M.A.; Newkome, G.R.;Selbin, J. J. Organomet. Chem., 1980, 202, 341-350; and 30: refs. 13 and 14 .
22. 3): δ 145.9; 128.5; 127.2; 127.0; 64.1; 62.9; 35.0; 32.0;25.6; 17.7; 3.0; 2.4. Calculated %C 83.53 %H 9.51. Found %C 83.62 %H 9.39. Three compounds are already known: :11a: Sashida, H.; Tsuchiya, T. Chem. Pharm. Bull. 1984, 32, 4117-4123; 22: Gutierrez, M.A.; Newkome, G.R.; Selbin, J. J. Organomet. Chem., 1980, 202, 341-350; and 30: refs. 13 and 14 .