77970-17-3Relevant articles and documents
3-NITROCYCLOALKENONES, SYNTHESIS AND USE AS REVERSE AFFINITY CYCLOALKYNONE EQUIVALENTS
Corey, E. J.,Estreicher, Herbert
, p. 603 - 606 (1981)
A partical synthesis of 3-nitrocycloalkenones and their utilization as dienophiles in the Diels-Alder reaction are discribed.The results demonstrate a reverse affinity equivalency between these β-nitro-enones and "cycloalkynones".
Allylic C-H activations using Cu(II) 2-quinoxalinol salen and tert-butyl hydroperoxide
Li, Yuancheng,Lee, Tae Bum,Wang, Tanyu,Gamble, Audrey V.,Gorden, Anne E. V.
experimental part, p. 4628 - 4633 (2012/08/08)
Using a Cu(II) 2-quinoxalinol salen complex as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant, allylic activations of olefin substrates can be converted to the corresponding enones or 1,4-enediones. Excellent yields can be achieved (up to 99%) within a very short reaction time and with great tolerance for additional functional groups. Possible mechanistic pathways have been characterized using Raman spectroscopy, cyclic voltammetry, and theoretical calculations.
An unprecedented method for the generation of tert -butylperoxy radical using DIB/TBHP protocol: Solvent effect and application on allylic oxidation
Zhao, Yi,Yeung, Ying-Yeung
supporting information; experimental part, p. 2128 - 2131 (2010/08/05)
Figure presented Tert-Butylperoxy radical was generated with PhI(OAc) 2 and tBuOOH. Ester solvent was found to be critical and the protocol was applied in the allylic oxidation of various olefinic substrates, which gave the corresponding α,β-unsaturated enones in good yield and regioselectivity.
Allylic Oxidations Catalyzed by Dirhodium Catalysts under Aqueous Conditions
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Page/Page column 10, (2009/04/24)
The present invention relates to compositions and methods for achieving the efficient allylic oxidation of organic molecules, especially olefins and steroids, under aqueous conditions. The invention concerns the use of dirhodium (II,II) “paddlewheel complexes, and in particular, dirhodium carboximate and tert-butyl hydroperoxide as catalysts for the reaction. The use of aqueous conditions is particularly advantageous in the allylic oxidation of 7-keto steroids, which could not be effectively oxidized using anhydrous methods, and in extending allylic oxidation to enamides and enol ethers.
Dirhodium(II) caprolactamate: An exceptional catalyst for allylic oxidation
Catino, Arthur J.,Forslund, Raymond E.,Doyle, Michael P.
, p. 13622 - 13623 (2007/10/03)
The oxidation of organic molecules represents a fundamentally important chemical process. Particularly important is allylic oxidation, whereby a single methylene unit is converted directly into a carbonyl group. In this communication, we report that dirhodium(II) caprolactamate [Rh2(cap)4] in combination with tert-butyl hydroperoxide (terminal oxidant) effectively catalyzes the allylic oxidation of a variety of olefins and enones. The reaction is completely selective, tolerant of air/moisture, and can be performed with as little as 0.1 mol % catalyst in minutes. A mechanistic proposal involving redox chain catalysis has been put forth, as well as evidence for the intermediacy of a higher valent dirhodium tert-butyl peroxy complex. Copyright
A SIMPLE SYNTHESIS OF 3-NITROCYCLOALKENONES AND THEIR ACETALS
Vankar, Yashwant D.,Bawa, Anita
, p. 1253 - 1256 (2007/10/02)
Synthesis of 3-nitrocyclohexenone and 3-nitrocycloheptenone and their acetals is described starting from cyclohexanone and cyclopentanone respectively.
