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 applying of actual the way 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 type of brief sj'nopses.Thanks are as a result of the Editorial Board, the writer, and the authors for his or her cooperation.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 11
F. Semmelhack, R. B. Hornby, and J. C. Vederas, Chem. Commun. 686 (1968). 122 123 T. SEC. 111. lZ6Other photochemical rearrangements are FeC14- phQ-cHs Ph Ph Ph (136) (135) Ph (137) also best interpreted as arising via an initial ringe cleavage. In this way, the conversion of 2,3-dihydro-5,6-dimethylpyrazineinto 1,4,5trimethylimidazole in 70% yield by photolysis in ethanol probably involves the intermediate diimine which undergoes rapid cyclization to the imidazole [Eq. F. Durst, Can. J . Cfiern.
111. F. S. T. REID enlargement and 2,3-diphenyl-6,7,8,g-tetrahydro-BH-imidazo[1,2-u]azepine (139) is obtained. l~~ This is believed to be the result of an initial disproportionation reaction yielding hexahydroand tetrahydro-2,4,6-triphenyl-s-triazine. ”YN+ Ph “YN Ph (140) L’”Z ph)(Nyph H Ph Ph (141) + ”Y” Ph (142) F. HETEROAROMATIC SYSTEMS A number of reports of photochemical decomposition of heteroaromatic compounds have appeared in the literature during the past 50 or 60 years. A few of these undoubtedly involve photooxidative processes, whereas others have been examined in the vapor phase, often a t elevated temperatures.
667 (1966). T. Janjiki, H. Kato, and M. Ohta, Chem. Commun. 496 (1968). 78 P. Dowd, J . Am. Chem. SOC. 88, 2587 (1966). 7 9 C. 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.
Advances in Heterocyclic Chemistry, Vol. 11 by A.R. Katritzky, A.J. Boulton (Eds.)