Oxalyl chloride
Name Reactions
Recent Literature
1-Vinylpyrroles are formylated by the N,N-dimethylformamide/oxalyl
chloride reagent system to give the corresponding 1-vinylpyrrole-2-carbaldehydes
in good yields in short reaction times.
A. I. Mikhaleva, A. V. Ivanoc, E. V. Skital'tseva, I. A. Ushakov, A. M.
Vasil'tsov, B. A. Trofimov, Synthesis, 2009,
587-590.
Highly regio- and stereoselective reactions of readily available
2-(methoxycarbonyl)-2,3-allenols with oxalyl chloride in the presence of Et3N
or DMSO afforded methyl 2-(ethynyl)alk-2(E)-enoates and
2-(1′-chlorovinyl)alk-2(Z)-enoates, respectively, in good yields.
Y. Deng, X. Kin, C. Fu, S. Ma, Org. Lett., 2009,
11, 2169-2172.
"Activated" dimethyl sulfoxide efficiently dehydrogenates hydrazones to the
respective diazo compounds at -78°C. Under optimized conditions, simple vacuum
filtration provides solutions of pure diazo compounds from which stable diazo
species can be isolated in high yield, or that can be directly used in
subsequent reactions.
M. I. Javed, M. Brewer, Org. Lett., 2007,
9, 1789-1792.
The use of oxalyl chloride with a catalytic amount of dimethyl sulfoxide in the
presence of Et3N enables the preparation of nitriles from primary amides or aldoximes
within 1 h at room
temperature. A diverse range of nitriles were obtained in good to
excellent yields, including aromatic, heteroaromatic, cyclic, and acyclic
aliphatic compounds.
R. Ding, Y. Liu, M. Han, W. Jiao, J. Li, H. Tian, B. Sun, J. Org. Chem., 2018, 83,
12939-12944.
