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: 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 how you can pyrrole chemistry and a truly 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 a result of Editorial Board, the writer, and the authors for his or her cooperation.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 11
G. Overberger and C. Yaroslavsky, Tetrahedron Letters 4395 (1965). ] THE PHOTOCHEMISTRY OF HETEROCYCLES 25 trans-1,5-diphenylpent-l-ene. 80 O-CO-CZHB “Y P h q P ‘h/ N=N Ph HPh A similar type of photoinduced ring cleavage is reported for diazirines, which have mostly been studied in the gas phase. Diazirine itself in the presence of nitrogen or a hydrocarbon is decomposed to methylene and nitrogen [Eq. s2 A variety of products are formed from disubstituted diazirines. O]hexane, and these can be interpreted as arising by an intramolecular process from an intermediate carbene G.
H. Barrett, R. P. Spitz, and R. Pitcher, J . Am. Chem. 87, 3417 (1965). 109 J. Holovka and P. D. Gardner, J . Am. Chem. SOC. 89, 6370 (1967). 110 W. G. Dauben and R. L. Cargill, Tetrahedron 12, 186 (1961). 111 R. Srinivasan, J . Am. Chem. SOC. 84, 3432 (1962). van Tamelen and D. Carty, J . Am. Chem. SOC. 89, 3922 (1967). Barton, Helv. Chim. Acta 42, 2604 (1959). 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).
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).