By A.R. Katritzky, A.J. Boulton (Eds.)
(from preface)This, the 11th quantity of Advances in Heterocyclic Chemistry, contains surveys of the chemistry of the next teams of heterocyclic compounds: benzothiophenes (B. Iddon and R. M. Scrow-ston), naphthyridines (W. W. Paudler and T. J. Kress), and quinu-clidines (L. N. Yakhontov). furthermore, R. A. Jones covers the appliance of actual easy methods to pyrrole chemistry and a truly topical topic, the photochemistry of heterocycles, is reviewed through S. T. Reid.Suggestions are welcomed for contributions to destiny volumes; they need to be within the kind of brief sj'nopses.Thanks are because of the Editorial Board, the writer, and the authors for his or her cooperation.
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 11
84 R. A. Moss, Tetrahedron Letters 4905 (1967). 85 R. A. Mitsch, J . Am. Chem. SOC. 87, 758 (1965). 86 G. L. Closs, W. A. Boll, H. Heyn, and V. Dev, J . Am. Chem. SOC. 90, 173 (1968). 111. ] 27 THE PHOTOCHEMISTRY OF HETEROCYCLES parallel in the previously reported photocyclization of diazoalkenes to the corresponding cyclopropenes. An interesting example of solvent dependence is observed in this reaction. O]pent-Z-ene (103); this isomerization is reversible, the 3H-pyrazole being regenerated at room temperature.
Am. Chem. SOC. 86, 950 (1964). Padwa and R. Hartman, J . Am. Chem. 86, 4212 (1964). de Mayo and S. T. Reid, Quart. Rev. (London)15,393 (1961). S. Becker and J. Michl, J . Am. Chem. SOC. 88, 5931 (1966). 119 R. Exelby and R. Grinter, Chem. Rev. 65, 247 (1965). Hirshberg, and E. Fischer, J . Chem. SOC. 156 (1961). 1 2 1 J. King, P. de Mayo, E. Morkved, A. B. M. A. Sattar, and A. Stoessl, Can. J . Chem. 41, 100 (1963). E. S. T. REID derivative (133). Recent studies lZ2 using flash photolysis have cast doubt on the existence of an intermediate sulfene (134).
130 Ring cleavage also occurs in pyridine, but the photochemical step in this case appears to be the photosensitized addition of water to pyridine, rather than direct carbon-nitrogen bond cleavage; an acyclic product is formed when the photolysis is carried out in basic solution [Eq. 131 Of greater interest, however, is the extent to which the photochemistry of a heteroaromatic system parallels that of benzene and its derivatives. Pyrazine (143 ; R = H) and 2-methylpyrazine (143 ; R = CH3) undergo photoisomerization both in the vapor phase and in solution with light of 253 nm wavelength to yield pyrimidine (144; R 1 = R 2 = R 3 = H ) ,and a mixture of 4-methyl- (144; R1=CH3, R 2 = R 3 = H ) ,5-methyl- (144; R 2 = C H 3R1 = R 3 = H ) ,and probably 2-methyl-pyrimidine (144; R3= CH,, R1 = R 2= H), r e s p e c t i ~ e 1 y .
Advances in Heterocyclic Chemistry, Vol. 11 by A.R. Katritzky, A.J. Boulton (Eds.)