Synthesis of 4-, 5-, and 6-methyl-2,2'-bipyridinyls
2,2'-Bipyridinyls continue to attract appreciable attention with practical applications ranging from effective herbicides to important ligands of great interest for chelation of transition metals, the ruthenium complexes being useful for photochemical generation of hydrogen from water and in chemically modified electrode studies. Unambiguous syntheses of 4-, 5- and 6-methyl-2,2'-bipyridinyls from the appropriate ..cap alpha..-oxoketene dithioacetals and the enolate of a suitable carbonyl compound are described. Two choices exist for the synthesis of a 2,2'-bipyridinyl by this route: the reaction of 2-acetylpyridine with an appropriately functionalized ..cap alpha..-oxoketene dithioacetal or, conversely, the reaction of an ..cap alpha..-oxoketene dihioacetal derived from 2-acetylpyridine with the enolate of an appropriate carbonyl compound. 16 references, 3 figures, 1 table.
- Research Organization:
- Rensselaer Polytechnic Institute, Troy, NY
- OSTI ID:
- 5814849
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 50:25; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ACETALS
ALCOHOLS
AZINES
BIPYRIDINES
CARBONYLS
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
DATA
ENOLS
ETHERS
EXPERIMENTAL DATA
HETEROCYCLIC COMPOUNDS
HYDROXY COMPOUNDS
INFORMATION
ISOMERS
KETENES
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PYRIDINES
STEREOCHEMISTRY
SULFUR COMPOUNDS
SYNTHESIS
YIELDS