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). additionally, R. A. Jones covers the applying of actual how 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 type 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
Lss The same transformation has been observed in norbornadiene, and other intramolecular cycloadditions are known [see, for example, Eq. (50) ls7]. An intermediate of this type has been postulated ls8 to account for the photorearrangement of 1,4-epoxy1,4-dihydronaphthalene to benz[f]oxepin [Eq. (51)]. hv. l~~ The two major products are the 1,4-dimer and the pentacyclic derivative (213), arising presumably by intramolecular photocycloaddition 186 E. Payo, L. Cortb, J. Mantecbn, C. Rivas, and G. de Pinto, Tetrahedron Letters 2415 (1967).
Horner, Ann. C h m . 614, 4 (1958). P. 30 S. T. REID [SEC. 111. E. products is rationalized in terms of a diradical intermediateg7[Eq. (27)]. 98 Ph hv Ph hv __f E. HETEROCYCLIC DIENES One of the many photoreactions of conjugated dienes is the formation of cyclobutenes,99and this has been reported both in cyclic and acyclic dienes. lOO This photoreaction is frequently observed in heterocyclic systems. A number of azacycloheptadienes are photochemically isomerized, in an identical manner to cycloheptadiene itself, to bicyclic derivatives.
Yamada, Tetrahedron Letters 4519 (1968). 169 C. Kaneko, I. Yokoe, and M. Ishikawa, Tetrahedron Letters 5237 (1967). 1 7 O 0. Buchardt, Tetrahedron Letters 1911 (1968). 167 168 M. SEC. lsOA few photoreactions, which are obviously related to those described above for heteroaromatic N-oxides. have been reported. These include the photolysis 171, 172 of certain pyridinium ylides to give lH-1,2-diazepine derivatives [Eq. (46)], and the photolysis 171 of pyridinium dicyanomethide [Eq. (47)]. IV. Photoaddition to Heterocycles Photoaddition to heterocyclic systems occurs both as a result of excitation of the heterocycle or of the species undergoing addition.