By A. R. Katritzky, A. J. Boulton
During this quantity 3 of the chapters take care of particular ring platforms: 1,2,3-triazoles (T. L. Gilchrist and G. E. Gymer), dibenzothiophenes (J. Ashby and С. С Cook), and the 7-azabicyclo[2.2.1]heptadienes, and their decreased, and benzo-fused, derivatives (L. J. Kricka and J. M. Vernon). 3 extra chapters conceal specific elements of heterocyclic compounds mostly: cationic cycloaddition reactions (С. К. Bradsher), homolytic fragrant substitution (F. Minisci and nil. Porta), and base-catalyzed hydrogen alternate (of ring protons) (J. A. Elvidge, J. R. Jones, zero. O'Brien, E. A. Evans, and H. C. Sheppard).
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 16
R. R. Rao, Rao,JJ .. Org. Org. Chem. Chem. 9. Org. Synth. 37, 3 7 ,26 2 6 (1957). (1957). E. Lieber, 72 E. Lieber, Lieber, C. N. R. Rao, Rao, and and T. T. V. V. Rajkumar, Rajkumar, JJ. Org. Chem. Chem. 24, 24, 134 134 (1959). (1959). 7ZE. Org. 73 A. Dornoa and H. Hell, Hell, Chem. Ber. Ber. 93, 93, 1998 1998 (1960). (1960). 73 74 H. Bojarska-Dahlig, Rec. Trav. Chim. 80, 80, 1348 1348 (1961). (1961). 74 75 G. G. L’abb6 L’abb6 and A. A. Hassner, J. Heterocycl. Heterocycl. Chem. Chem. 7, 7, 361 361 (1970).
Kirova, and Yu. M. Kapustin, Reakts. Sposobnost Org. Soedin. 5 , 806 (1968). 54 55 Sec. 1 BASE-CATALYZED HYDROGEN EXCHANGE 21 sources. ^? Reference has previously been made52,53 to the likely existence of a carbanion intermediate in the dehydrohalogenation of 3-halopyridines in liquid ammonia. 0) shows that a considerable amount of negative charge (carbanion character) is generated in the transition state of these isotope exchange reactions. It is interesting that the same equation also correlates the rates of exchange a t the meta and para positions of monosubstituted benzenes, so that a common mechanism for both benzenes and pyridines seems likely.
L. Bell, J . Heterocycl. Chem. 3 , 4 4 0 (1966). 7013 I. Fletcher, A. J. Boulton, and A. 71 T. J. Curphey, J . Amer. Chem. Soc. 72 [Sec. B. J. A. ELVIDOE ET A L . 26 2-position in 1,3-dimethy1-4-pyrimidonium iodide (70) is much faster than its unquaternized analog. The more recent work of Beak and Bonham70 has confirmed that exchange of the 2-H of l-methyl-4pyrimidone takes place by deuteroxide-catalyzed attack on the pyrimidonium ion (71) leading to an ylide intermediate (Scheme 11). 0 I CH, (71) 0 I CH, 0 I CH, SCHEME 11 Exchange of the 5-H of uridine (72, R 1= H, R, = OH, R3 = H, X = 0) in slightly basic DzO a t 60" using 2-mercaptoethylamine as base has been reported.
Advances in Heterocyclic Chemistry, Vol. 16 by A. R. Katritzky, A. J. Boulton