Identification o f a Baker-type Mechanism in Additions to p-Nitrophenyl Isothiocyanate in Diethyl Ether Solution

D M U R'NCO + RNH, ^ R ‘N = C —CT 2> R'NHCONHR (1) I + NH, I R 1 rearrangement. Subsequent work has shown that this type of mechanism is not, in fact, satisfactory for alcoholysis, and that a mechanism in which nucleophilic attack and proton transfer are concerted, and involve associated nucleophile, is likely [3, 4, 5]. Such a mechanism [equation (2) —(3)] also provides a better explanation of existing kinetic findings for aminolysis [3].