Helvetica Chimica Acta p. 1204 - 1216 (1985)
Update date:2022-07-30
Topics:
Phaff, Rox
Bischofberger, Norbert
Mathies, Peter
Petter, Walter
Frei, Bruno
Jeger, Oskar
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)-O bond of the oxirane, respectively.The structures of the products 22-25, 27, and 28 were assigned on the basis of the spectral data of the photolysis products of the 13C-labelled diepoxyketone <6,6-dimethyl-13C2>-3 and by X-ray analysis of the compounds 24 and 35, the latter being the p-nitrobenzoate of 22.
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