1907-65-9Relevant articles and documents
A new practical one-pot access to sulfonimidates
Leca, Dominique,Fensterbank, Louis,Lacote, Emmanuel,Malacria, Max
, p. 4093 - 4095 (2002)
(matrix presented) Sulfonimidates were prepared from sulfinamides and iodosobenzene in a very mild one-pot procedure in good to excellent yields. This reaction allows quick and efficient access to a class of molecules of important synthetic as well as biological and industrial interest.
Synthesis, crystal structure, optical, electrochemical and thermal properties of the ynamide: Bis-(N-4-methylbenzenesulfonyl, N-n-butyl)-1,3-butadiyne-1,4-diamide
Doan, Thu-Hong,Talbi, Imen,Lohier, Jean-Fran?ois,Touil, Soufiane,Alayrac, Carole,Witulski, Bernhard
, p. 127 - 134 (2016)
The novel ynamide compound, bis-(N-4-methylbenzenesulfonyl, N-n-butyl)-1,3-butadiyne-1,4-diamide (3), was synthesized and characterized by single crystal X-ray diffraction, 1H and 13C NMR, UV-fluorescence spectroscopy, cyclic voltammetry, TGA and DSC techniques. This first reported X-ray structure of a 1,3-butadiyne-1,4-diamide revealed that the amido substituents of 3 adopt a twisted conformation in the crystal with a torsion angle of 76.6° resulting in a molecule with axial chirality. The crystal structure of compound 3 is stabilized by intermolecular CH-π interactions that give pairs of stacked bis-alkyne-3 units. HOMO/LUMO energy levels of 3 were experimentally determined by means of electrochemical and optical methods to be??5.87/?1.98?eV respectively. The solid state polymerization of the title compound was investigated by differential scanning calorimetry (DSC) revealing that polymerization proceeded simultaneously to the phase transition assigned to the melting of 3. The solid state polymerization of 3 is discussed of being a topochemically initiated polymer chain reaction that proceeds with a non-topochemical chain growth.
Au(I)-Catalyzed Oxidative Functionalization of Yndiamides
Tong, Zixuan,Garry, Olivia L.,Smith, Philip J.,Jiang, Yubo,Mansfield, Steven J.,Anderson, Edward A.
supporting information, p. 4888 - 4892 (2021/06/28)
Yndiamides, underexplored cousins of ynamides, offer rich synthetic potential as doubly nitrogenated two carbon building blocks. Here we report a gold-catalyzed oxidative functionalization of yndiamides to access unnatural amino acid derivatives, using a wide range of nucleophiles as a source of the amino acid side chain. The transformation proceeds under mild conditions, is highly functional group tolerant, and displays excellent regioselectivity through subtle steric differentiation of the yndiamide nitrogen atom substituents.
Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation
Shi, Shasha,Yang, Xianyu,Tang, Man,Hu, Jiefeng,Loh, Teck-Peng
, p. 4018 - 4022 (2021/05/26)
Herein, we disclose a transition-metal-free reaction system that enables α-cyanation of sulfonamides through C-H bond cleavage for the preparation of α-amino nitriles, including difficult-to-access all-alkyl α-tertiary scaffolds. More than 50 substrate examples prove a wide functional group tolerance. Additionally, its synthetic practicality is highlighted by gram-scalability and the late-stage modification of natural compounds. Mechanistic experiments suggest that this process involves in situ formation of an imine intermediate via base-promoted elimination of HF.