153524-64-2Relevant academic research and scientific papers
Generation of α-Radicals of Acetic Acid Derivatives from α-Stannyl Ester and Amide and Their Reactions with Electron-Rich Olefins
Kohno, Yasushi,Narasaka, Koichi
, p. 1689 - 1692 (1993)
Oxidation of α-tributylstannyl ester and amide with CeIV compounds generates α-radicals of acetic acid derivatives with the elimination of the stannyl group.The radicals thus generated react with various electron-rich olefins to give the corresponding addition products in good yield.
Synthesis and characterization of poly(ε-caprolactone-co-δ- valerolactone) with pendant carboxylic functional groups
Zeng, Yue,Zhang, Yan,Lang, Meidong
experimental part, p. 343 - 350 (2012/01/13)
In this paper, aliphatic polyesters functionalized with pendant carboxylic groups were synthesized via several steps. Firstly, substituted cyclic ketone, 2-(benzyloxycarbonyl methyl)cyclopentanone (BCP) was prepared through the reaction of enamine with benzyl-2-bromoacetate, and subsequently converted into the relevant functionalized δ-valerolactone derivative, 5-(benzyloxy carbonylmethyl)-δ-valerolactone (BVL) by the Baeyer-Villiger oxidation. Secondly, the ring-opening polymerization of BVL with ε-caprolactone was carried out in bulk using stannous octoate as the catalyst to produce poly(ε-caprolactone-co-δ-valerolactone) bearing the benzyl-protected carboxyl functional groups [P(CL-co-BVL)]. Finally, the benzyl-protecting groups of P(CL-co-BVL) were effectively removed by H2 using Pd/C as the catalyst to obtain poly(ε-caprolactone-co-δ-valerolactone) bearing pendant carboxylic acids [P(CL-co-CVL)]. The structure and the properties of the polymer have been studied by Nuclear Magnetic Resonance (NMR), Fourier Infrared Spectroscopy (FT-IR) and Differential Scan Calorimetry (DSC) etc. The NMR and FT-IR results confirmed the polymer structure, and the 13C NMR spectra have clearly interpreted the sequence of ε-caprolactone and 5-(benzyloxycarbonylmethyl)-δ-valerolactone in the copolymer. When the benzyl-protecting groups were removed, the aliphatic polyesters bearing carboxylic groups were obtained. Moreover, the hydrophilicity of the polymer was improved. Thus, poly(ε-caprolactone-co-δ-valerolactone) might have great potential in biomedical fields. Copyright
Cascade radical reactions catalyzed by a Pd/light system: Cyclizative multiple carbonylation of 4-alkenyl iodides
Ryu, Ilhyong,Kreimerman, Sergio,Araki, Fumikazu,Nishitani, Satoshi,Oderaotoshi, Yoji,Minakata, Satoshi,Komatsu, Mitsuo
, p. 3812 - 3813 (2007/10/03)
Cascade reactions of 4-alkenyl iodides, involving a carbonylation-cyclization-carbonylation sequence, were accomplished by a hν/Pd system. The stereochemical outcomes suggest that radical carbonylation and subsequent acyl radical cyclization may be involv
Oxidative Generation of α-Radicals of Carbonyl Compounds from the α-Stannyl Derivatives and Their Reactions with Electron-Rich Olefins
Kohno, Yasushi,Narasaka, Koichi
, p. 322 - 329 (2007/10/02)
The oxidation of α-tributylstannyl alkanoates with tetrabutylammonium hexanitratocerate(IV) generates α-radicals of the alkanoates by eliminating the stannylium ion.The thus-formed radicals react with various electron-rich olefinic compounds, such as silyl enol ethers, giving addition products in good yield.This method formally achieves selective cross coupling between alkanoates and ketones.
