Sulfilimine

Examples include S,S-diphenylsulfilimine[2] and sulfoximines [Category] such as methylphenylsulfoximine:[3] 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.

These compounds are typically prepared by oxidation of thioethers with electrophilic amine reagents, such as chloramine-T in the presence of a base:[4] An alternative route involves reactions of electrophilic sulfur compounds with amines.

[5] KMnO4 can oxidize sulfilimines to sulfoximines, but the latter are more generally produced from addition of azides to sulfoxides.

[5] Sulfilimine bonds stabilize collagen IV strands found in the extracellular matrix[6] and arose at least 500 mya.

[7] These bonds covalently connect hydroxylysine and methionine residues of adjacent polypeptide strands to form a larger collagen trimer.