40674-15-5Relevant academic research and scientific papers
Metal-Free Cross-Dehydrogenative C-O Coupling of Carbonyl Compounds with N-Hydroxyimides: Unexpected Selective Behavior of Highly Reactive Free Radicals at an Elevated Temperature
Krylov, Igor B.,Lopat'Eva, Elena R.,Budnikov, Alexander S.,Nikishin, Gennady I.,Terent'Ev, Alexander O.
supporting information, p. 1935 - 1947 (2020/02/04)
Cross-dehydrogenative C-O coupling of N-hydroxyimides with ketones, esters, and carboxylic acids was achieved employing the di-tert-butyl peroxide as a source of free radicals and a dehydrogenating agent. The proposed method is experimentally simple and demonstrates the outstanding efficiency for the challenging CH substrates, such as unactivated esters and carboxylic acids. It was shown that N-hydroxyphthalimide drastically affects the oxidative properties of t-BuOOt-Bu by intercepting the t-BuO radicals with the formation of phthalimide-N-oxyl radicals, a species responsible for both hydrogen atom abstraction from the CH reagent and the selective formation of the C-O coupling product by selective radical cross-recombination. The practical applicability of the developed method was exemplified by the single-stage synthesis of commercial reagent (known as Baran aminating reagent precursor) from isobutyric acid and N-hydroxysuccinimide, whereas in the standard synthetic approach, four stages are necessary.
Alkylation of Allyl/Alkenyl Sulfones by Deoxygenation of Alkoxyl Radicals
Han, Jia-Bin,Guo, Ao,Tang, Xiang-Ying
supporting information, p. 2989 - 2994 (2019/02/05)
A challenging deoxygenation of alkoxyl radicals from readily accessible alcohol derivatives was developed, affording facile synthesis of functionalized alkenes with good functional group tolerance under mild reaction conditions. Because alkoxyl radicals can easily undergo β-fragmentations or hydrogen abstractions, this new strategy for deoxygenation of alkoxyl radicals is highly valuable. Moreover, mechanistic studies revealed that the electron-neutral phosphine acts as the deoxygenation reagent.
Effect of optically active ethyl 2-phthalimidooxypropionate on the growth of cress, lepidium sativum
Takekida, Yukinori,Okazaki, Momotoshi,Shuto, Yoshihiro
, p. 1831 - 1833 (2007/10/03)
The effects of 2-phthalimidooxyalkanoic acid derivatives on the germination and root-growth of cress were examined. Since 2-phthalimidooxypropionates were most effective, the optically active ethyl esters were prepared. As the result of biological testing, the (S)-(+)-isomer exhibited stronger activity than the (R)-(+)-isomer. This result is contrary to those from commercial herbicides with similar structures, phenoxy- and oxyphenoxy-propionate-type compounds, where the (R)-isomers are generally known to be the active principles.
Synthesis and Anticonvulsant Activity of Imidooxy Derivatives
Edafiogho, Ivan O.,Scott, K. R.,Moore, Jacqueline A.,Farrar, Vida A.,Nicholson, Jesse M.
, p. 387 - 392 (2007/10/02)
Previous results of anticonvulsant activity in several imidooxy carboxylates related to (aminooxy)acetic acid in young chicks, prompted an in-depth reinvestigation of these analogues in mice.A series of 22 succinimidooxy, phthalimidooxy, and naphthalimido
