69305-79-9

Upstream product

• 109-89-7 diethylamine 
• 698-16-8 benzohydroximoyl chloride 
• 932-90-1 Benzaldoxime 

Downstream Products

• 888-71-1 3,5-diphenyl-1,2,4-oxadiazole 
• 20594-92-7 3,5-diphenyl-1,2,4-oxadiazole-4-oxide 
• 5585-14-8 3,4-diphenyl-furazan 2-oxide 
• 61713-81-3 3,5-bis(p-tolyl)-1,2,4-oxadiazole-4-oxide 
• 186665-02-1 5-phenyl-3-p-tolyl-1,2,4-oxadiasole-4-oxide 
• 188118-29-8 3,5-bis(4-methoxyphenyl)-1,2,4-oxadiazole 4-oxide 
• 188118-33-4 3-anisyl-5-phenyl-1,2,4-oxadiazole-4-oxide 
• 61713-85-7 3,5-bis(p-chlorophenyl)-1,2,4-oxadiazole 4-oxide 
• 188118-34-5 3-(4-Chloro-phenyl)-5-phenyl-[1,2,4]oxadiazole 4-oxide 
• 61713-82-4 3,5-bis(p-nitrophenyl)-1,2,4-oxadiazole 4-oxide 
• 188118-35-6 3-(4-Nitro-phenyl)-5-phenyl-[1,2,4]oxadiazole 4-oxide 
• 55667-07-7 3,5-bis(4-methoxyphenyl)-1,2,4-oxadiazole 
• 75273-66-4 3-(4-methoxyphenyl)-5-phenyl-1,2,4-oxadiazole 

Relevant academic research and scientific papers

Cycloadditions of nitrile oxides to amidoximes. A general synthesis of 3,5-disubstituted 1,2,4-oxadiazole-4-oxides

The cycloaddition of nitrile oxides to amidoximes is a general method for the synthesis of 3,5-disubstituted 1,2,4-oxadiazole-4-oxides with the same or different substituents. The yields are only moderate since an equivalent amount of the nitrile oxide is consumed by reaction with the amine released in the fragmentation of the primary cycloadducts and reforms the amidoxime. With excess nitrile oxides the 1,2,4-oxadiazole-4-oxides undergo a disproportionation reaction to yield nitroso carbonyl intermediates and 1,2,4-oxadiazoles.

CONFIGURATION AND CONFORMATION OF AMIDOXIMES. N,N-DIALKYL DERIVATIVES

Dipole moments of N,N-dialkylamidoximes Ia-Ie and of substituted O-benzoyl-N,N-dimethylbenzamidoximes IIa-IIe were measured in benzene or dioxan, respectively.The results with the later set of compounds allow to assign in an independent and unambiguous way the E-configuration which was found previously for all N,N-dialkylamidoximes investigated in the crystalline state; our reasoning does not involve bond moment values within the amidoxime functional group.The fundamental difference in the stereochemistry between unsubstituted amidoximes and their N,N-dialkyl derivatives has been confirmed.On the other hand, the configuration of simple N,N-dialkylamidoximes (e.g.Ia-Ie) cannot be deduced from their dipole moments in a straightforward manner.The reason is that the conjugation within the N=C-N chain requires a mesomeric correction term which cannot be neglected and is not equal in either configuration.The example shows very clearly limitations of the bond moment approach if applied to conjugated molecules.