Contra-thermodynamic trans-esteripication of carbamates by counter-attack strategy: A viable non-phosgene, non-mic route to carbamate pesticides

Article abstract of DOI:10.1016/S0040-4020(01)86381-X

Treatment of methyl N-methylcarbaaate (1, R= Me) with phosphorus oxychloride and 1-naphthol results in the formation of the transesterified product, 1-naphthyl N-methylcarbamate (2, Ar=1-naphthy 1) in good yield. Similarly, ethyl N-methylthiocarbamate (5) is converted to 1-naphthyl N-methylcarbamate (2, Ar= 1-naphthyl) on treatment with phosphorus oxychloride and 1-naphthol. The mechanism of these interesting and industrially important transformations is discussed.