Tetraethylammonium bromide catalysed phase transfer reaction of potassium superoxide with hydrazones and tosylhydrazones

A variety of hydrazones and tosylhydrazones of carbonyl compounds have been investigated under the mild reaction conditions of potassium superoxide an d tetraethylammonium bromide in dry dimethylformamide. As a result, hydrazo nes are generally transformed to their corresponding azines whereas tosylhy drazones undergo facile fragmentation to give the olefinic products in fair ly good yields. The study highlights the use of tetraethylammonium bromide as an efficient and inexpensive catalyst for superoxide studies.