By R. A. Abramovitch
Chapter I half A. homes and Reactions of Pyridines (pages 1–135): R. A. Abramovitch and G. M. Singer
Chapter I half B. in part lowered Pyridines (pages 137–182): Robert E. Lyle
Chapter II man made and usual assets of the Pyridine Ring (pages 183–307): N. S. Boodman, J. O. Hawthorne, P. X. Masciantonio and A. W. Simon
Chapter III Quaternary Pyridinium Compounds (pages 309–430): Oscar R. Rodig
Read Online or Download Chemistry of Heterocyclic Compounds: Pyridine and its Derivatives, Supplement, Part One, Volume 14 PDF
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Additional resources for Chemistry of Heterocyclic Compounds: Pyridine and its Derivatives, Supplement, Part One, Volume 14
Relative Reactivitiesof Pyridine, 3-Picobe.
Homolytic arylation of pyridines has been studied extensively (271-275). Protonation of the ring nitrogen has the effect of activating C-2 toward homolytic arylation relative to C-4 (276-278). Partial rate factors have been determined for the arylation of pyridines. Pyridine is arylated slightly more readily than is benzene by phenyl radicals (271, 279), more readily by Chemical Reactivity 43 TABLE L4-3. Total Rate Ratios in the Gomberg-HeyArylation of Pyridine at 40" (281) -K XC, H,. XC,H,. '6% Ph.
2-Amino-3-methylpyridine undergoes exchange as the conjugate acid: - 2-Amino-S-chloropyridine and 5chloro-2dimethylaminopyridine react as the free base at acidities less than Do = -2, and as the conjugate acids at higher acidities. A recent study revised the old finding (230, 231) that only 0-alkylation occurred in the reaction of 2-pyridone with diazomethane. The N-methyl isomer is actually the major product (232). The reaction of diazomethane with 6-hydroxy-2-pyridone gives, in addition to the expected N-and 0-alkylation products, a novel hydrazone (IA-34) which results from electrophilic substitution at C-3 (233).