M. Ali et Dpn. Satchell, KINETICS AND MECHANISM OF THE HYDROLYSIS OF 2-(4-METHOXY-PHENYL)-1,3-DITHIANE IN AQUEOUS PERCHLORIC-ACID, Journal of chemical research. Synopses, (3), 1993, pp. 114-115
In concentrated (7-9 mol dm-3) aqueous perchloric acid, 2-aryl-1,3-dit
hianes normally hydrolyse to give a high yield of aldehyde and propane
-1,3-dithiol in a two-stage process via an initially formed equilibriu
m mixture of aldehyde, dithiol, hemithioacetal and unreacted dithiane;
kinetic studies using especially 2-(4-methoxyphenyl)-1,3-dithiane (I)
suggest that these relatively unreactive cyclic dithioacetals lead to
the hemithioacetal by an A2 mechanism.