3006-86-8Relevant articles and documents
Neutral Organic Super Electron Donors Made Catalytic
Rohrbach, Simon,Shah, Rushabh S.,Tuttle, Tell,Murphy, John A.
supporting information, p. 11454 - 11458 (2019/07/18)
Neutral organic super electron donors (SEDs) display impressive reducing power but, until now, it has not been possible to use them catalytically in radical chain reactions. This is because, following electron transfer, these donors form persistent radical cations that trap substrate-derived radicals. This paper unlocks a conceptually new approach to super electron donors that overcomes this issue, leading to the first catalytic neutral organic super electron donor.
Synthesis of geminal bisperoxides by acid-catalyzed reaction of acetals and enol ethers with tert-butyl hydroperoxide
Terent'ev, Alexander O.,Kutkin, Alexander V.,Troizky, Nikolay A.,Ogibin, Yuri N.,Nikishin, Gennady I.
, p. 2215 - 2219 (2007/10/03)
A new efficient procedure was developed for the synthesis of geminal bisperoxides by reaction of ketals and enol ethers with tert-butyl hydroperoxide catalyzed by protic or Lewis acids. Georg Thieme Verlag Stuttgart.
Radical Intermediates in the Thermal Decomposition of 1,1-Bis(t-butyldioxy)cyclohexane
Sugihara, Yasushi,Watanabe, Yasumasa,Kumura, Hiromi,Nakamura, Tomoyuki,Suyama, Shuji,Sawaki, Yasuhiko
, p. 664 - 667 (2007/10/02)
The thermolysis mechanism of 1,1-bis(t-butyldioxy)cyclohexane (6) has been studied in solutions.The activation parameters obtained in cumene are ΔH=139.5 kJ mol-1 and ΔS=44.8 J K-1 mol-1, and the volatile products are t-butyl alcohol, t-butyl peroxyhexanoate, and 2,3-dimethyl-2,3-diphenylbutane along with minor products of acetone, cyclohexanone, and t-butyl 1-methyl-1-phenylethyl peroxide.The thermolysis of 6 in benzene gave acetone and t-butyl alcohol as major volatile products.The polyester of 2-hydroxyhexanoic acid was obtained both in cumene and benzene as a non-volatile product, and the yield was as high as 76percent in benzene.These facts indicate that oxyl radical (7) undergoes a facile ring-opening reaction yielding 5-(t-butyldioxycarbonyl)pentyl radical (8).The resulting radicals abstract hydrogen atoms either intra- or intermolecularly.The former reaction is predominant in the absence of good hydrogen donors, affording 2-hexanolide and ultimately the corresponding polyesters.