SYNTHESIS OF THIOCYANATE AND ISOTHIOCYANATE SUBSTITUTED CARBONATES AND CARBAMATES

Article abstract of DOI:10.1016/S0040-4020(01)86723-5

Reactions of alkyl 1-chloroethyl carbonates 1 and 1-chloroethyl N,N-dialkyl carbamates 2 with MSCN (M=K, NH4) in acetone or in protic solvents (MeOH, HCONH2) afforded the corresponding thio- and/or isothiocyano derivates in good yields.The origin of the N-bonded compounds is discussed and it is concluded that most of these compounds must be due to a N condensation of the thiocyanate anion.During this work, we also found a new very mild method for isomerizing in good yields alkyl 1-thiocyanoethyl carbonates and 1-thiocyanoethyl N,N-dialkyl carbamates to their corresponding isothiocyano derivates.