Journal of the Chemical Society. Perkin transactions I p. 2363 - 2368 (1994)
Update date:2022-08-05
Topics:
Aggarwal, Varinder K.
Davies, Ian W.
Franklin, Richard
Maddock, John
Mahon, Mary F.
Molloy, Kieran C.
Oxidation of 1,3-dithiane has been carried out using eight different oxidants under several different reaction conditions.The most favourable conditions for obtaining the required trans-1,3-dithiane 1,3-dioxide were to use either MCPBA in Et2O or NaIO4 in MeOH-H2O.Other 5,5-disubstituted-1,3-dithianes were also prepared and subjected to similar oxidations.For these compounds the best oxidant for obtaining the trans-dioxides was O3.A rationalisation for the stereochemical outcome of the oxidations is presented and required that trans-1,3-dithiane 1,3-dioxide is more stable than cis-1,3-dithiane 1,3-dioxide.This is borne out by equilibration studies of the two diastereoisomeric sulfoxides using N2O4.A rationalisation for the greater stability of the trans compared to the cis isomer is also presented and fits with the pKa values and melting points of the two compounds.
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