29927-85-3Relevant articles and documents
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Gutsche,C.D. et al.
, p. 1782 - 1790 (1967)
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Tolstikov,G.A. et al.
, (1975)
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Reductive radical cyclization of cyclic γ-cyanoketones promoted by samarium(II) iodide without photoirradiation
Kakiuchi, Kiyomi,Fujioka, Yasunari,Yamamura, Hirohisa,Tsutsumi, Ken,Morimoto, Tsumoru,Kurosawa, Hideo
, p. 7595 - 7598 (2001)
Reaction of cyclic γ-cyanoketones with 3 equiv. of SmI2 in the presence of t-BuOH as a proton source in HMPA-THF without photoirradiation gave the desired α-hydroxycycloalkanones along with overreduced ketones after hydrolysis. In the absence of t-BuOH, the formation of the overreduced ketones was depressed and the yields of the α-hydroxyketones increased, while the reaction proceeded slowly.
N,N-Dideuterated Alkylamines from N-Benzylidenealkylamines. Improved Lithium/Ethylamine Reduction of α,β-Unsaturated Ketones
Burgstahler, Albert W.,Sanders, Mark E.
, p. 400 - 402 (1980)
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Regio- and stereoselective cyclization reactions of unsaturated silyl enol ethers by photoinduced electron transfer - Mechanistic aspects and synthetic approach
Hintz, Sandra,Mattay, Jochen,Van Eldik, Rudi,Fu, Wen-Fu
, p. 1583 - 1596 (2007/10/03)
Oxidative photoinduced electron transfer (PET) reactions have been performed with various silyl enol ethers and silyloxy-2H-chromones bearing an olefmic or silylacetylenic side chain. The reactions result in regioselective ring closure with the formation of bi- to tetracyclic ring systems with a well-defined ring juncture, e.g. perhydrophenanthrenones 13 or benzo-annellated xanthenones 24. Our investigations have focussed on the optimization of this cychzation method with regard to irradiation time and product yield. The irradiation times could be reduced by using the cosensitized PET method. Modifying the substrate at the silyl group led to enhanced yields. In addition, we found that solvent and pressure dependences are important tools, allowing control of the regiochemistry. Both the synthesis of 6-endo products by radical cationic reaction pathways, as well as 5-exo ring closure by radical intermediates was achieved. Mechanistic details, including findings from deuterium labelling experiments, are discussed.
Ruthenium-Catalyzed Oxidation of Nonactivated Alcohols by MnO2
Karlsson, Ulrika,Wang, Guo-Zhi,Baeckvall, Jan-E.
, p. 1196 - 1198 (2007/10/02)
Nonactivated alcohols are oxidized to ketones by MnO2 in the presence of a catalytic system consisting of 2 (1) and 2,6-di-tert-butylbenzoquinone (2).The reaction proceeds via a ruthenium-catalyzed dehydrogenation of the alcohol and subsequent hydrogen transfer to 2,6-di-tert-butylbenzoquinone (2).The hydroquinone formed is reoxidized to quinone by MnO2.
