Sulfenamide

Additionally primary as well as secondary and tertiary amines form sulfenamides through reaction with, thiols, disulfides, and sulfenyl thiocyanates.

[3] In one illustrative synthesis, triphenylmethanesulphenyl chloride and butylamine react in benzene at 25 C: Many other routes to sulfenamides are known, starting from thiols and disulfides.

The existence of these distinct stereoisomers is due to the formation of a partial double bond between either sulfur or nitrogen's lone pair and the other atom's antibonding orbitals.

These lone pairs allow for the possibility of forming either higher order bonds(double, triple) or adding new substituent groups to the compound.

[2] Sulfenamides react with amino-azaheterocycles to form heterocyclic systems (often used as amino protecting groups in various other synthesis reactions).

Additionally in the traditional Apple reaction, the R-OH bond is cleaved leaving oxygen attached to triphenylphosphine.