Photochemical reactions. 145th Communication. Carbonyl vs. epoxyketone photochemistry: Photolysis of 1, 2; 3, 4??diepoxy??2, 6, 6??trimethyl??1??cyclohexyl methyl …

…, N Bischofberger, P Mathies, W Petter…

Index: Phaff, Rox; Bischofberger, Norbert; Mathies, Peter; Petter, Walter; Frei, Bruno; Jeger, Oskar Helvetica Chimica Acta, 1985 , vol. 68, p. 1204 - 1216

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Abstract

Abstract The synthesis and photolysis of the title compound 3 is described. Irradiation (λ> 280 nm, MeCN) of the di-epoxyketone 3 leads predominantly to γ–H abstraction. Cyclization furnishes the cyclobutanols 22–24, while cleavage gives compound 25, presumably via the allene-oxide intermediate 36. Further, products 27 and 28 are formed by Norrish fragmentation and by initial cleavage of the C (α)[BOND] O bond of the oxirane, ...