799804-23-2Relevant articles and documents
Straightforward and highly efficient synthesis of α-acetoxy ketones through gold-catalyzed intermolecular oxidation of terminal alkynes
Wu, Chao,Liang, Zhiwu,Yan, Dong,He, Weimin,Xiang, Jiannan
, p. 2605 - 2611 (2013/09/24)
A variety of terminal alkynes were efficiently converted into the corresponding α-acetoxy ketones through gold-catalyzed intermolecular oxidation in the presence of 8-methylquinoline 1-oxide as the oxidant. The reaction probably proceeds through an α-oxo gold carbene intermolecular O-H insertion.
Photochemical preparation of highly functionalized 1-indanones
Wessig, Pablo,Glombitza, Clemens,Mueller, Gunnar,Teubner, Janek
, p. 7582 - 7591 (2007/10/03)
A series of o-alkylphenyl alkyl ketones 1 were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-π* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo-[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.
