DTBB-Catalyzed lithiation of 2,6-bis(chloromethyl)pyridine

Arkivoc

Volumn 2005, Issue 9, 2004, Pages 10-20

  Gómez, Cecilia ^a   Maciá, Beatriz ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

2,6 Bis(lithiomethyl)pyridine; DTBB catalyzed lithiation; Electrophilic substitution; Tridentate ligands

Indexed keywords

2,6 BIS(2 ETHYL 2 HYDROXYBUTYL)PYRIDINE; 2,6 BIS(2 HYDROXY 3,3 DIMETHYLBUTYL)PYRIDINE; 2,6 BIS(2 HYDROXY 4 METHYLPENTYL)PYRIDINE; 2,6 BIS(2 HYDROXYBICYCLO[2.2.1]HEPT 2 YLMETHYL)PYRIDINE; 2,6 BIS(2 METHYL 2 HYDROXYPROPYL)PYRIDINE; 2,6 BIS(2 PROPYL 2 HYDROXYPENTYL)PYRIDINE; 2,6 BIS(CHLOROMETHYL)PYRIDINE; 2,6 BIS[(1 HYDROXYCYCLOHEXYL)METHYL]PYRIDINE; 2,6 BIS[(1 HYDROXYCYCLOPENTYL)METHYL]PYRIDINE; 4,4' DI TERT BUTYLBIPHENYL; BIPHENYL DERIVATIVE; CARBONYL DERIVATIVE; NORBORNANE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROLYSIS; ISOLATION PROCEDURE; LITHIATION; METHODOLOGY; PURIFICATION; REACTION ANALYSIS; ROOM TEMPERATURE; TEMPERATURE;

EID: 15444368898     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

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33. For polymer versions of this reaction, see: (a) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron Lett. 1998, 39, 1397. (b) Gómez, C.; Ruiz, S.; Yus, M. Tetrahedron. 1999, 55, 7017. (c) Yus, M.; Candela, P.; Gómez, C. Tetrahedron 2002, 58, 6207. (d) Arnauld, T.; Barret, A. G. M.; Hopkins, B. T. Tetrahedron Lett. 2002, 43, 1081.
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38. 15c- extrusion, see: (b) Takemura, H.; Shinmyozu, T.; Inazu, T. Tetrahedron Lett. 1988, 29, 1031. (c) Martel, H. J. J.-B.; Rasmussen, M. Tetrahedron Lett. 1971, 3843. (d) X-ray analysis: Pahor, N. B.; Calligaris, M.; Randaccio, L. J. Chem. Soc., Perkin Trans. 2 1978, 38.
39. 15c- extrusion, see: (b) Takemura, H.; Shinmyozu, T.; Inazu, T. Tetrahedron Lett. 1988, 29, 1031. (c) Martel, H. J. J.-B.; Rasmussen, M. Tetrahedron Lett. 1971, 3843. (d) X-ray analysis: Pahor, N. B.; Calligaris, M.; Randaccio, L. J. Chem. Soc., Perkin Trans. 2 1978, 38.
40. 15c- extrusion, see: (b) Takemura, H.; Shinmyozu, T.; Inazu, T. Tetrahedron Lett. 1988, 29, 1031. (c) Martel, H. J. J.-B.; Rasmussen, M. Tetrahedron Lett. 1971, 3843. (d) X-ray analysis: Pahor, N. B.; Calligaris, M.; Randaccio, L. J. Chem. Soc., Perkin Trans. 2 1978, 38.
41. Compound 3 has been prepared (25% yield) by treatment of 2,6-bis(bromomethyl)pyridine with phenyllithium: (a) Boekelheide, V.; Lawson, J. A. J. Chem. Soc., Chem. Commun. 1970, 1558. For other sophisticated routes involving nitrogen15b- or sulfur15c- extrusion, see: (b) Takemura, H.; Shinmyozu, T.; Inazu, T. Tetrahedron Lett. 1988, 29, 1031. (c) Martel, H. J. J.-B.; Rasmussen, M. Tetrahedron Lett. 1971, 3843. (d) X-ray analysis: Pahor, N. B.; Calligaris, M.; Randaccio, L. J. Chem. Soc., Perkin Trans. 2 1978, 38.
42. This type of compound shows interest related to the structure of pentacoordinated organosilane derivatives. See, for example, ref. 7c.
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