3152-68-9Relevant articles and documents
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Gettler,Hammett
, p. 1824,1825 (1943)
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An Expedient Synthesis of α,β-Unsaturated Ketones Using Nitroalkenes and Sulfones
Awen, Bahlul Z.,Miyashita, Masaaki,Shiratani, Tomonori,Yoshikoshi, Akira,Irie, Hiroshi
, p. 767 - 768 (1992)
A facile synthesis of various substituted α,β-unsaturated ketones utilizing nitroalkenes and sulfones are described, in which conjugate addition of sulfonyl carbanions to nitroalkenes, ozonolysis or acid treatment of the resulting lithium nitronates and subsequent elimination of sulfinic acid from keto sulfones by DBU are involved.
Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide
Matsumoto, Shoji,Marumoto, Hayato,Akazome, Motohiro,Otani, Yasuhiko,Kaiho, Tatsuo
, p. 590 - 599 (2021/03/29)
The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.
A Heck reaction/photochemical alkene isomerization sequence to prepare functionalized quinolines
Donohoe, Timothy J.,Hoff, Oskar,Hoffman, Jack B.,Kelly, Alex,Walker, Johannes C. L.,Werrel, Simon
, (2020/08/06)
A route to prepare functionalized quinolines based on a Heck reaction/UV-induced alkene isomerization sequence is described. The method allows for the preparation of quinolines under mild and neutral conditions and has broad functional group tolerance. Acid-sensitive functional groups that would not be tolerated under previous approaches can be included and a one-pot quinoline forming procedure is also reported.
Additive-Free Isomerization of Allylic Alcohols to Ketones with a Cobalt PNP Pincer Catalyst
Spiegelberg, Brian,Dell'Acqua, Andrea,Xia, Tian,Spannenberg, Anke,Tin, Sergey,Hinze, Sandra,de Vries, Johannes G.
supporting information, p. 7820 - 7825 (2019/05/22)
Catalytic isomerization of allylic alcohols in ethanol as a green solvent was achieved by using air and moisture stable cobalt (II) complexes in the absence of any additives. Under mild conditions, the cobalt PNP pincer complex substituted with phenyl groups on the phosphorus atoms appeared to be the most active. High rates were obtained at 120 °C, even though the addition of one equivalent of base increases the speed of the reaction drastically. Although some evidence was obtained supporting a dehydrogenation–hydrogenation mechanism, it was proven that this is not the major mechanism. Instead, the cobalt hydride complex formed by dehydrogenation of ethanol is capable of double-bond isomerization through alkene insertion–elimination.
