Advances in Heterocyclic Chemistry, Volume 61 by Alan R. Katritzky

By Alan R. Katritzky

Tested in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area-one of serious significance to natural chemists, polymer chemists, and such a lot organic scientists. each 5th quantity ofAdvances in Heterocyclic Chemistry includes a cumulative topic index.

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Albert, R. J. Goldacre, and J. N. Phillips, J . Chem. 2240 (1948). 36 w. ADRIEN ALBERT AND L. F. ARMAREGO [Sec. IV. which 2-aminopyrazine resonance is stronger than 2-aminopyridine resonance can perhaps be judged by the difference in the pK values between these 2-amino derivatives and the parent substances, vix. 6, respectively. 6. Oxygen anion resonance. This means of stabilizing hydration depends on the resonance shown in 39b-c, which is akin to 2,4dihydroxypyridine anion resonance. g. 24) is mentioned in Section III,E, 1,d.

The only abnormal spectrum 55-57 seems to be that of the anion of 2-mercaptopurine which is being further examined. This does not exclude the possibility that hydration occurs too rapidly t o be detected with existing apparatus. Special point is given to t,his conclusion by a recent survey of 8 - a ~ a p u r i n e sThe . ~ ~abnormal 53 W. A. D. Thesis, Princeton University, 1963; personal communication from Prof. E. C. Taylor (1963). 5 4 A. Albert and D. J. Brown, J . Chem. SOC. 2060 (1954). 55 D.

Chem. SOC. 6062 (1960). 36 Sec. 111. 21 COVALENT HYDRATION: I. 5 x (determined as described in the following review lo), but the derivatives have somewhat different values depending on the position and nature of the substituent. 8 x and 10 x respectively, indicating the electronattracting property of the nitro group. g. g. 13 Two important exceptions are now discussed. Substituents in the 4-position, whether -I or +I,have a strong dehydrating effect (cf. Section 11,C). e. in position 7) to the carbon atom C-4, the tendency to hydrate is strongly reduced.

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