By Alan R. Katritzky
Verified in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area-one of serious value to natural chemists, polymer chemists, and so much organic scientists. each 5th quantity ofAdvances in Heterocyclic Chemistry incorporates a cumulative topic index.
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5 6 G. B. Elion, J . Org. Chem. 27, 2478 (1962). 57 S. F. Mason, J . Ghem. SOC. 2071 (1954). 58 A. Albert and D. D. Perrin, unpublished results (1963). Sec. ] COVALENT HYDRATION : I. QUALITATIVE ASPECTS 33 ultraviolet spectrum and pK, value indicated that the 8-azapurine cation is hydrated. Ready oxidation with acidified hydrogen peroxide to 6-hydroxy-8-azapurine proved that the 1,6-double bond in 8-azapurine is the site of hydration. 2-Hydroxy-8-azapurine was shown by rapid-reaction techniques (see Section 11,E) t o be anhydrous in the anion and hydrated in the neutral species.
Osborn, K. Schofield, and L. N. Short,J. Soc. 4191 (1956). 37 A. Albert, Chem. SOC. (London) Spec. Publ. No. 3, 138 (1955). 38 D. J. Fry, J. D. Kendall, and A. J. Morgan, J . 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.
G. the ureatype resonance and the 4-aminopyridine-type resonance in 2- and 6-hydroxypteridine, respectively. g. g. 43. Thus far, this section has been concerned with the explanation of the factors responsible for the covalent hydration of heteroaromatic substances. g. the dihydropyridines, 61 W. L. F. Armarego, J . Chem. 6073 (1963). 38 ADRIEN ALBERT AND W. L. F. ARMAREGO [Sec. V. dihydropyrans, and dihydropyrroles) add water much more readily, but this behavior is far less remarkable. 62The similarity between these two processes resides in the conversion of an aromatic ring into a nonaromatic ring bearing a secondary alcohol group.
Advances in Heterocyclic Chemistry, Vol. 4 by Alan R. Katritzky