Cleavage of C=N derivatives and oxidation of thiols in water under neutral conditions with 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bischloride

Article abstract of DOI:10.3184/030823407X240890

1,4-Diazabicyclo[2,2,2]octane (DABCO) is easily chlorinated and gives a complex which efficiently converts aliphatic and aromatic oximes, phenylhydrazones and semicarbazones to their corresponding carbonyl compounds in water at 50°C in high yield. This reagent can also be used for conversion of thiols to their compounding disulfide under the same reaction conditions. DABCO is quantitatively recovered which can be rechlorinated and reused several times.