The proposed mechanism is supported by several observations. The fact that the reaction is catalyzed by acids and inhibited by bases is consistent with the protonation of the amine as a rate-determining part of the mechanism. Second,the aliphatic amine-based benzoxazines undergo COLBERT reactions much more readily then their aromatic counterparts. Aromatic amines are less basic than the aliphatic amines [24], and as such would not be as readily protonated by the thiol to initialize the reaction. Also, when there is a competing reaction, the COLBERT reaction proceeds more readily in polar solvents, such as methanol and DMSO than in chloroform, solvents that would stabilize the ammonium cation intermediate (Figure 14).