Tetrahedron Letters

Efficient solid state photocyclization of sterically congested α-o-tolyl ketones despite “poor” geometries for hydrogen abstraction

PJ Wagner, B Zhou

文献索引：Wagner, Peter J.; Zhou, Boli Tetrahedron Letters, 1989 , vol. 30, # 40 p. 5389 - 5392

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被引用次数: 8

摘要

Abstract 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 ...