The Preparation of Aliphatic Fluorinated Sulfoximines

Abstract

This work describes the preparation of an aliphatic series of the N-trifluoromethanesulfonyl-S-trifluoromethyl-S-sulfoximine group. The key step of the synthesis is the imination of fluorinated sulfoxides under experimental conditions, which avoid cleavage of the alkyl group. The formation of sulfoximines 6 and 15 allows the preparation of various fluorinated sulfoximines having strong electron withdrawing properties.

Keywords

fluorine - sulfur - arylations - sulfoximines - imination of sulfoxides

References and Notes

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10

We assume that the lack of reactivity is due to the poor nucleophilicity of the sulfur because of the presence of the trifluoromethyl group.

12

Attempts at imination of sulfoxide 5 under Yagupol’skii’s conditions gave rise to a complex mixture of products in a low yield. In Bentley and Whitehead’s conditions no transformation of the fluorinated sulfoxide 5 was observed.