By A. R. Katritzky
(from preface)The current quantity comprises 5 chapters, 3 of that are on topics formerly lined in those advances.The photochemistry o( oxygen- and sulfur-containing heterocycles is complementary to the evaluation at the photochemistry oi' nitrogen heterocycles that seemed in quantity 30: jointly those chapters replace an prior evaluate of the photochemistry of heterocycles (all via S. T. Reid). which seemed in 1970 in quantity II. Paudler and Sheets have up-to-date their evaluation of the overall chemistry o( naphthyridines, which additionally seemed in quantity II. furthermore, van der Plas. Wo/niak. and van den Haak have in particular thought of the reactions of naphthyridines with nitrogen nueleophiles. principally from their very own large investigations during this area.Hermecv and Mes/aros have surveyed the chemistry of pyrido| l.2-| pyrimidines (and have integrated 469 references). the single previous assessment that covers the literature as much as 1957 indexed an insignificant forty three references. eventually, Timpe and Rl'tsov have handled the large topic of pseudoa/.u-lenes, outlined in a huge method to disguise a wide selection o\' hicyclic heterocycles.
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 33
REID been proposed to account for the photochemically induced conversion of the sulfoxide (281) to the disulfide (282)231; the ketone group does not, in this case, appear to have any influence on the reactivity. l]non-6-en-2-one (286)233 ; the products are shown in Scheme 23. d Gi,, C0,Me SCHIMI:23 4. Seven-Membered and Larger Heterocycles Relatively few examples of photoreactions of seven-membered and larger heterocycles have been reported. The major products of irradiation of liquid oxepin are hex-5-en-1-01 and h e ~ a n a l photodecomposition ~~~; of cyclic ethers has, in general been shown to be largely dependent on ring size.
Kumar and K . S. Sidhu, /ridimi J . Cheni. 11, 899 (1973). R. C. Petlerson, A. L. Herbert, G. W. Griffin, I . Sarkar, 0. P. Strausz, and J. Font, J . lrrocycl. ('hem. 10, 879 (1973). T. Fujisawa and T. Kobori, Japan Kokai 74142677 [ C A 81, 135999 (1974jl. U. Jacobsson, T. Kempe, and T. Norin, J . OrR, C ' / i w i . 39, 2722 (1974). L. A . -W. Chen, J . A m . CYicvii. Sor. 101, 390(1979j. J . G . Etcifici and C. Diehert, J . Ani. Cliern. Soc. 91, 4595 (1969). J . P. Wosacz, M. M. Joullie, U. Mende, 1.
M . Tokuda, V. V. Chung, A. Suzuki, and M. Itoh, J . Org. C ' / W ~ I ,40, 1858 (1975); V . V. Chung, M. Tokuda, A. Suzuki. and M. Itoh, Bull. Chenr. Soc. Jpn. 49, 341 (1976). V. T. Ramakrishnan a n d J. Kagan. J . C h i . 35, 2898 (1970). Sec. B] OXYGEN- A N D SULFUR-CONTAININGHETEROCYCLES 23 to products 121 and 122, as shown in Scheme 8. l o 2 Ring opening of the oxiran is not stereospecific, and the same two products are obtained on irradiation of the epimeric oxiran. lo3 Me M e Me M e Me (124) 0' (125) Decarbonylation is observed.