Tetrahedron Letters p. 5389 - 5392 (1989)
Update date:2022-08-04
Topics:
Wagner, Peter J.
Zhou, Boli
Several α-mesityl and α-(o-tolyl)acetophenones undergo photocyclization to 2-indanols almost quantitatively when irradiated as crystals, even those that undergo significant competing α-cleavage or 1,3-aryl shift in solution.The requisite triplet δ-hydrogen abstraction apparently can occur at what appears to be a "bad" geometry.One ketone, α-(o-tolyl)propiophenone, partially rearranges to the β-isomer, which arises from disproportionation of the radicals formed by initial α-cleavage.
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