2510-60-3Relevant academic research and scientific papers
Visible Light-Induced Iodine-Catalyzed Transformation of Terminal Alkynes to Primary Amides via C≡C Bond Cleavage under Aqueous Conditions
Dighe, Shashikant U.,Batra, Sanjay
supporting information, p. 500 - 505 (2016/02/12)
The visible light-induced iodine-catalyzed oxidative cleavage of the C≡C bond for transforming terminal alkynes into primary amides in the presence of ammonia under aqueous conditions is described. This metal-free protocol which ensued via initial hydroamination of the acetylene bond followed by liberation of diiodomethane (CH2I2) was found to be applicable to aromatic, heteroaromatic and aliphatic alkynes.
A palladium-catalyzed carbonylative route to primary amides
Morera, Enrico,Ortar, Giorgio
, p. 2835 - 2838 (2007/10/03)
The palladium-catalyzed reaction of aryl and vinyl iodides and triflates with carbon monoxide in the presence of hexamethyldisilazane followed by hydrolytic work-up affords aromatic and α,β-unsaturated primary amides in good to high yields under relatively mild conditions.
Conformations, spectroscopy, and photochemistry of methyl phenanthrene-9-carboxylate, phenanthrene-9-carboxamides, and their Lewis acid complexes
Lewis, Frederick D.,Barancyk, Steven V.,Burch, Eric L.
, p. 3866 - 3870 (2007/10/02)
The spectroscopic properties and photochemical behavior of methyl phenanthrene-9-carboxylate and of a primary, secondary, and tertiary phenanthrene-9-carboxamides have been investigated in the absence and presence of strong Lewis acids. The ground-state conformations of the free and complexed molecules have been investigated by means of NMR and Gaussian 88 calculations. The dihedral angle between the phenanthrene and the carbonyl group is found to be dependent upon the bulk of the 9-substituent and upon Lewis acid complexation. Complexation also changes the secondary amide conformation from syn to anti. Both the phenanthrenes and their complexes are strongly fluorescent. Equilibrium constants for complex formation have been determined by means of fluorescence titrations. Rate constants for both radiative and nonradiative singlet-state decay increase upon complexation. The nonradiative rate constants for several boron halide complexes display a heavy-atom effect, which is larger for tertiary vs primary amides. Complexation results in an increase in both ester and amide singlet-state reactivity with simple alkenes.
