41126-02-7Relevant academic research and scientific papers
A Double Ionic Mechanism for the Chapman-like Rearrangement of Imino-ethers to N-Alkylamides, in the Solid State or in the Melt. Theoretical and Experimental Evidence
Dessolin, Michele,Eisenstein, Odile,Golfier, Michel,Prange, Thierry,Sautet, Philippe
, p. 132 - 134 (1992)
Using 5-methoxy-2-aryl-1,3,4-oxadiazoles as models it was shown that the thermal rearrangement of imino-ethers to N-alkylamides proceeds through a double ionic mechanism; kinetics measurements in the solid state and in the melt give apparent activation energies that support ab initio calculated activation enthalpies.
I2 mediated synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones via sequential condensation/oxidative cyclization and rearrangement
Patel, Shyam Sunder,Chandna, Nisha,Kumar, Shreemoyee,Jain, Nidhi
, p. 5683 - 5689 (2016/07/06)
A simple and efficient iodine-assisted protocol for the synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones has been developed. The reaction involves a sequential condensation followed by tandem oxidative cyclization and rearrangement of
Verdazyl radicals as substrates for organic synthesis: A synthesis of 3-methyl-5-aryl-1,3,4-oxadiazolones
Bancerz, Matthew,Georges, Michael K.
, p. 6377 - 6382 (2011/10/05)
The synthesis of oxadiazolones under hydrolytic conditions is described for a series of 3-methyl-5-aryl-1,3,4-oxadiazolone compounds. The unique starting materials for the hydrolysis reaction are obtained from efficient 1,3-dipolar cycloaddition reactions
An Unusually Fast Chapman-like Thermal Rearrangement in the Solid State
Dessolin, Michele,Golfier, Michel
, p. 38 - 39 (2007/10/02)
Some 5-methoxy-2-aryl-1,3,4-oxadiazoles undergo a 1,3 O-to-N thermal rearrangement of the methyl group, which takes place unusually easily, and much faster in the solid state than in the melt.
