Sulfilimine
In chemistry, a sulfilimine is a type of chemical compound containing a sulfur-to-nitrogen bond which is often represented as a double bond. In fact, a double bond violates the octet rule, and the bond may be considered a single bond with a formal charge of +1 on the sulfur and a formal charge of −1 on the nitrogen. The parent compound is sulfilimine, which is mainly of theoretical interest.
Examples include S,''S''-diphenylsulfilimine and sulfoximines such as methylphenylsulfoximine:
In the case of a sulfoximine, the bonds can be considered single bonds, with formal charges of −1 on both the oxygen and the nitrogen, and a formal charge of +2 on the sulfur.
Preparation
Most sulfilimines are N-substituted with electron-withdrawing groups. These compounds are typically prepared by oxidation of thioethers with electrophilic amine reagents, such as chloramine-T in the presence of a base:An alternative route involves reactions of electrophilic sulfur compounds with amines. The imidosulfonium reagents provide a source of "", which are attacked by amines.
In general, aliphatic sulfilimines, unsubstituted at N, are not stable above.
KMnO4 can oxidize sulfilimines to sulfoximines, but the latter are more generally produced from addition of azides to sulfoxides.