24331-71-3Relevant articles and documents
INTERRELATIONS OF THE ENERGETICS OF AMIDES AND ALKENES: ENTHALPIES OF FORMATION OF N,N-DIMETHYL DERIVATIVES OF PIVALAMIDE, 1-ADAMANTYLCARBOXAMIDE AND BENZAMIDE, AND OF STYRENNE AND ITS α-, TRANS-β AND β,β-METHYLATED DERIVATIVES
Abboud, Jose-Luis M.,Jimenez, Pilar,Roux, M. Victoria,Turrion, Concepcion,Lopez-Mardomingo, Carmen,et al.
, p. 15 - 25 (1995)
The enthalpies of formation of the condensed phase and gaseous N,N-dimethyl derivatives of pivalamide, 1-adamantylcarboxamide and benzamide were determined by combustion calorimetry and the associated enthalpies of vaporization and sublimation.The enthalpies of formation of styrene and its α-, trans-β- and β,β-methylated derivatives were determined from measurements of their enthalpies of hydrogenation in dilute hydrocarbon solution.Strain and resonance effects of amides and alkenes are discussed in terms of the exo-/endothermicity of the following reactions: CH3CONH2(g)+RC(CH3)=CH2 -> (CH3)2C=CH2(g)+RCONH2(g), CH3CON(CH3)2(g)+RCH=C(CH3)2(g) -> CH3CH=C(CH3)2(g)+RCON(CH3)2(g) and in terms of the difference of enthalpies of formation of the isomeric (Z)- and (E)-RCH=CHCH3.
Direct amidation of acid fluorides using germanium amides
Hayatifar, Ardalan,Elifritz, Emily A.,Bloom, Molly B.,Pixley, Kaitlyn M.,Fennell, Christopher J.,Weinert, Charles S.
supporting information, p. 4490 - 4493 (2021/04/12)
Amide functional groups are an essential linkage that are found in peptides, proteins, and pharmaceuticals and new methods are constantly being sought for their formation. Here, a new method for their preparation is presented where germanium amides Ph3GeNR2convert acid fluorides directly to amides. These germanium amides serve to abstract the fluorine atom of the acid fluoride and transfer their amide group -NR2to the carbonyl carbon, and so function as amidation reagents.
Iridium-Catalyzed Reductive Strecker Reaction for Late-Stage Amide and Lactam Cyanation
Fuentes de Arriba, ángel L.,Lenci, Elena,Sonawane, Mahendra,Formery, Odilon,Dixon, Darren J.
supporting information, p. 3655 - 3659 (2017/03/21)
A new iridium-catalyzed reductive Strecker reaction for the direct and efficient formation of α-amino nitrile products from a broad range of (hetero)aromatic and aliphatic tertiary amides, and N-alkyl lactams is reported. The protocol exploits the mild and highly chemoselective reduction of the amide and lactam functionalities using IrCl(CO)[P(C6H5)3]2 (Vaska's complex) in the presence of tetramethyldisiloxane, as a reductant, to directly generate hemiaminal species able to undergo substitution by cyanide upon treatment with TMSCN (TMS=trimethylsilyl). The protocol is simple to perform, broad in scope, efficient (up to 99 % yield), and has been successfully applied to the late-stage functionalization of amide- and lactam-containing drugs, and naturally occurring alkaloids, as well as for the selective cyanation of the carbonyl carbon atom linked to the N atom of proline residues within di- and tripeptides.
Easy access to amides through aldehydic C-H bond functionalization catalyzed by heterogeneous Co-based catalysts
Bai, Cuihua,Yao, Xianfang,Li, Yingwei
, p. 884 - 891 (2015/02/19)
A novel synthesis strategy for amides by oxidative amidation of aldehydes is developed using a heterogeneous Co-based catalyst. The Co composite was prepared by simple pyrolysis of a Co-containing MOF, to obtain well-dispersed Co nanoparticles enclosed by carbonized organic ligands. The catalysts were characterized by powder X-ray diffraction (PXRD), N2 physical adsorption, atomic absorption spectroscopy (AAS), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), and X-ray photoelectron spectroscopy (XPS). The small Co nanoparticles embedded in the N-doped carbons were highly dispersed with an average size of ca. 7 nm. The Co@C-N materials exhibited significantly enhanced catalytic activity in the oxidative amidation of aldehydes in comparison to those of commercial sources. A series of amides can be easily obtained in good to excellent yields. It was found that the reaction proceeded via radicals under mild conditions, and the carbonyl group in the amide product was from the aldehyde. Moreover, the catalyst could be easily separated by using an external magnetic field and reused several times without significant loss in catalytic efficiency under the investigated conditions. (Chemical Equation Presented).