Thermal and Photolytic Decomposition of Tosylhydrazones of Cyclic Ketones Containing Sulfur Atom

Abstract

The thermal and the photolytic decomposition of tosylhydrazones of tetrahydro-4 H-thiopyran4-one [2] and dihydro-2 H-thiopyran-3(4 H)-one [4] were studied. In the thermal and the photolytic decomposition of [2] and [4] cyclic olefins were produced. In the case of [4], α, β-unsaturated olefin was predominated over β, γ-unsaturated one in the thermal decomposition in the presence of sodium hydride in diglyme and the photolytic decomposition in the presence of sodium in ethylene glycol, as shown in eqs. (6) and (9).
On the other hand, in the case of [2] the corresponding azine afforded as a major product in the thermal decomposition in the presence of sodium methoxide in ethylene glycol and the photolytic decomposition in the presence of sodium hydride in diglyme, as shown in eqs. (3) and (4).
The mechanism which may explain the formations of the observed products were discussed.