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.
α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp3)-H Coupling
Spangler, Jillian E.,Kobayashi, Yoshihisa,Verma, Pritha,Wang, Dong-Hui,Yu, Jin-Quan
supporting information, p. 11876 - 11879 (2015/10/05)
Pd(II)-catalyzed α-C(sp3)-H arylation of pyrrolidines, piperidines, azepanes, and N-methylamines with arylboronic acids has been developed for the first time. This transformation is applicable to wide arrays of pyrrolidines and boronic acids, including heteroaromatic boronic acids. A diastereoselective one-pot heterodiarylation of pyrrolidines has also been achieved.