Dichlorodiethyl sulfone explained

Dichlorodiethyl sulfone (or mustard sulfone) is an oxidation product of mustard gas. It has the formula (ClCH₂CH₂)₂SO₂. Although it is irritating to the eyes, it is not nearly as bad as mustard gas (dichlorodiethyl sulfide).^{[1] [2]}

Structure

The all-trans arrangement is predicted by Hartree-Fock computational methods to be the most stable conformer.^[3]

Reactions

When refluxed with aqueous sodium hydroxide, oxygen replaces the chlorine, and an 1,4-oxathiane ring is formed, p-oxathiane-4,4-dioxide.^[4] When treated with sodium carbonate, a weaker base, bis-(hydroxyethyl)sulfone is the major product formed.^[4] In comparison the dehydrochlorination of the sulfoxide is much slower.^[4]

Notes and References

1. Book: Lewis . Robert A. . Hawley's Condensed Chemical Dictionary . 2016 . John Wiley & Sons . 978-1-119-26784-3 . 452 . en.
2. Book: Transactions of the Annual Conference of State Sanitary Engineers . 1943 . 3–175 . en.
3. White . William E. . Sobus . Micah J. . Okerberg . Brian c. . Conformations Of Mustard Sulfoxide And Mustard Sulfone . Phosphorus, Sulfur, and Silicon and the Related Elements . November 1998 . 142 . 1 . 149–165 . 10.1080/10426509808029673.
4. Book: Breslow . David S. . David S. Breslow . Skolnik . Herman . Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles . 2009 . John Wiley & Sons . 978-0-470-18833-0 . 836 . en.