Sulfilimine


A sulfilimine is a type of chemical compound containing a sulfur-to-nitrogen double bond. The parent compound is sulfilimine H2S=NH, which is mainly of theoretical interest.
Examples include S,S-diphenylsulfilimine and :Category:Sulfoximines|sulfoximines such as methylphenylsulfoximine:
S,S-diphenylsulfilimine, a sulfur compound

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 limidosulfonium reagents provide a source of "Me2S2+", which are attacked by amines.

Sulfilimine bonds in proteins

Sulfilimine bonds stabilize collagen IV strands found in the extracellular matrix and arose at least 500 mya. These bonds covalently connect hydroxylysine and methionine residues of adjacent polypeptide strands to form a larger collagen trimer.