Advances in Heterocyclic Chemistry, Vol. 11 by A.R. Katritzky, A.J. Boulton (Eds.)

By A.R. Katritzky, A.J. Boulton (Eds.)

(from preface)This, the 11th quantity of Advances in Heterocyclic Chemistry, comprises surveys of the chemistry of the subsequent teams of heterocyclic compounds: benzo[6]thiophenes (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 really topical topic, the photochemistry of heterocycles, is reviewed by means of 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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87 88 cyclopropenes, but a mixture of 1,3-dienes (107) and allenes (108) in the ratio 2 :3. The formation of these photoproducts was shown to be intermolecular and involve the diazoester (109), which rapidly rearranges to the isomeric species (110) in preference to loss of nitrogen and carbene formation. The dienes and allenes are then directly formed from 110. 90The process is more specific than the corresponding thermal decomposition. Photolysis of cis-5-methyl-3,4diphenyl-1,2,3-triazoline(111) in cyclohexane solution gives pre(112) and only a little dominantly cis-3-rnethyl-l,2-diphenylaziridine of the trans isomer.

114 R. Srinivasan, Advan. Photochem. 4, 113 (1966). lle 4,6-Dimethyl-2-pyrone (128), however, undergoes ring cleavage on irradiation in methanol, 11' presumably via the intermediate ketene (129), to the unsaturated ester (130). Ring cleavage of this type has been proposed to account for 0 (128) (129) (130) the photochromism of a series of 2H-chromenes and 2 H - p ~ r a n s . l ~ ~ Colorless 2H-chromene itself is converted into the colored open-chain form [Eq. (30)] by irradiation at low temperature, and the process is thermally reversible, usually a t room temperature.

De Pinto, Tetrahedron Letters 2415 (1967). 187 C. M. Anderson, J. B. Bremner, I. W. McCay, and R. N. Warrener, Tetrahedron Letters 1255 ( 1968). 188 G. R. Ziegler and G. S. Hammond, J . Am. Chem. SOC. 90, 513 (1968). 189 A. I. Meyers and P. Singh, Tetrahedron Letters 4073 (1968).

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