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2,6-Di-tert-butylpyridine

2,6-Di-tert-butylpyridine is an organic compound with the formula (Me3C)2C5H3N. This colourless, oily liquid is derived from pyridine by replacement of the two H atoms with tert-butyl groups. It is a hindered base. For example, it can be protonated, but it does not form an adduct with boron trifluoride.

Preparation

2,6-Di-tert-butylpyridine is prepared by the reaction of tert-butyllithium with pyridine. The synthesis is reminiscent of the Chichibabin reaction.

Some related bulky pyridine compounds have been described, including 2,4,6-tri-t-butylpyridine and 2,6-di-tert-butyl-4-methylpyridine.

References

References

  1. Rafael R. Kostikov, Sánchez-Sancho Francisco, María Garranzo and M. Carmen Murcia "2,6-Di-t-butylpyridine" Encyclopedia of Reagents for Organic Synthesis 2010. {{doi. 10.1002/047084289X.rd068.pub2
  2. Edward Deutsch, Nai Kong V. Cheung "Noncoordinating buffers. I. Synthesis and characterization of water soluble derivatives of 2,6-di-tert-butylpyridine" ''J. Org. Chem.'' 1973, vol 38, pp 1123–1126. {{doi. 10.1021/jo00946a013
  3. Francis V. Scalzi, Norman F. Golob "Alkylation of pyridine with tert-butyllithium. Convenient syntheses of 2,6-di-tert-butylpyridine and 2,4,6-tri-tert-butylpyridine" ''J. Org. Chem.'' 1971, vol 36, pp 2541–2542 {{doi. 10.1021/jo00816a036. Hongmei Li "2,4,6-Tri-tert-butylpyridine" Encyclopedia of Reagents for Organic Synthesis 2004. {{doi. 10.1002/047084289X.rn00512
  4. Alexandru T. Balaban "2,6-Di-tert-butyl-4-methylpyridine (DTBMP)" Encyclopedia of Reagents for Organic Synthesis 2004. {{doi. 10.1002/047084289X.rn00509
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disubstituted-pyridines reagents-for-organic-chemistry non-nucleophilic-bases tert-butyl-compounds
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