23646-72-2Relevant academic research and scientific papers
Synthesis of amides using the Ritter reaction with bismuth triflate catalysis
Callens, Emmanuel,Burton, Andrew J.,Barrett, Anthony G.M.
, p. 8699 - 8701 (2007/10/03)
N-tert-Alkyl and aryl amides were obtained by a Ritter reaction of various nitriles with tertiary alcohols in the presence of a catalytic amount of bismuth triflate.
Sulfur mediated ritter reactions: The synthesis of cyclic amides
Eastgate, Martin D.,Fox, David J.,Morley, Thomas J.,Warren, Stuart
, p. 2124 - 2128 (2007/10/03)
Simple β-hydroxy-γ-phenylsulfanyl nitriles undergo a selective Ritter reaction, onto a thiiranium (episulfonium) ion, to yield 15-membered triamides. This selective trimerisation allows the rapid synthesis of these macrocylic triamides.
Intramolecular motions in a series of crystalline benzylammonium bromides and dibenzylamines studied by CP/MAS NMR
Riddell, Frank G.,Rogerson, Martin
, p. 493 - 504 (2007/10/03)
A series of 15 compounds including ammonium bromides containing one or two benzyl groups with H, methyl, isopropyl, tert-butyl and tert-amyl substituents and dibenzylamihe with N-isopropyl-, N-tert-butyl- and N-tert-amyl substituents have been synthesised and studied by CP/MAS NMR. The results of dynamic NMR studies on the solids suggest that there is a dramatically wide range of molecular motions occurring in this simple series of compounds: A combination of 2D CPEXSY, dynamic line shape analyses and T1ρ measurements reveals the considerable extent of intramolecular group motions including rotations of methyl, tert-butyl, tert-amyl and phenyl groups. Rates of rotation and activation parameters for these molecular motions are derived where appropriate. In the case of benzyl-tert-butylammonium bromide, where two independent molecules of the compound exist in the asymmetric unit it is shown that the independent processes of tert-butyl rotation in the two molecules have vastly different activation energies that differ by ca. 16 kJ mol-1. The extent of the motions observed suggests that commonly held prejudices about the rigidity of molecules in crystalline solids need revising.
On the synthesis of nitrilium salts from nitriles and chloroformates
Shrestha-Dawadi,Jochims
, p. 426 - 432 (2007/10/02)
Nitriles react with methyl or ethyl chloroformate (2a,b) and antimony(V) chloride to give high yields of N-methyl-, or N-ethylnitrilium hexachloroantimonates 3,4. With butyl chloroformate (2c) N-(1-methylpropyl)nitrilium salts 6 are obtained. These products arise from a 2-butyl cation, which is formed prior to alkylation of the nitrile. Isobutyl chloroformate (2d), (2-tert-butylcyclohexyl) chloroformate (2e), menthyl chloroformate (2f), 2,2-dimethylpropyl chloroformate (2g), and 3-methylbutyl chloroformate (2h) react with nitriles to give N-tert-alkylnitrilium salts, 11,13,15,19, which were characterized by hydrolysis to amides. With phenyl chloroformate (2i) benzonitriles react in a 1:2 ratio to furnish 2-phenoxy-1,3,5-oxadiazinium salts 21.
INSERTION OF BENZOYLNITRENE TOWARD HYDROCARBON C-H BONDS
Inagaki, Masao,Shingaki, Tadao,Nagai, Toshikazu
, p. 1419 - 1422 (2007/10/02)
Benzoylnitrene, generated photochemically from benzoyl azide, was inserted stereospecifically into the tertiary C-H bonds of cis- and trans-1,4-dimethylcyclohexanes.The insertion regioselectivities toward the C-H bonds were determided by use of 2-methylbutane and 2,3-dimethylbutane.The insertion proceeds involving the singlet nitrene, but not the triplet, and the photoCurtius rearrangement takes place independently of the nitrene reaction.
