82978-04-9Relevant articles and documents
Photolytic Conversion of Some Bicycloheptanones into 3-Hydroxy- or 3-Methoxy-2-oxabicyclooctan-2-ones
Newton, Roger F.,Reynolds, Derek P.,Crossland, Noelle M.,Kelly, David R.,Roberts, Stanley M.
, p. 1583 - 1586 (2007/10/02)
The ketones (1) and (7)-(9) gave the corresponding cyclic acetals (3), (4), and (12)-(17), respectively, on photolysis in methanol.Concurrent production of the alkenes (6) and (18)-(20) detracted from the potential synthetic utility of this process.However, photolysis of the ketones (8), (10), and (11) in aqueous tetrahydrofuran or aqueous acetonitrile led to a highly selective ring-expansion process, and consequently high yields of the corresponding γ-lactols (21)-(23).