Studies on the Oxidation of 1,3-Dithiane and 5,5-Disubstituted Analogues Including X-Ray Crystal Structure, Equilibration Studies and pKa Measurements on Selected Oxides

DOI: 10.1039/P19940002363

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2363 - 2368 (1994)

Update date:2022-08-05

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Authors:

Aggarwal, Varinder K.

Davies, Ian W.

Franklin, Richard

Maddock, John

Mahon, Mary F.

Molloy, Kieran C.

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Article abstract of DOI:10.1039/P19940002363

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 pK_a values and melting points of the two compounds.

Full text of DOI:10.1039/P19940002363

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