Phenyl-N-methyl-N-thiobenzoylcarbamate was prepared from the reaction of thiobenzamide anion with phenylchloroformate in DMF and kinetic data obtained for the basic hydrolysis, have been interpreted in terms of a BAc2 mechanism involving general bases catalysis.
References
1.
BruiceT.C., and BenkovicS. J., Bioorganic Mechanism, Benjamin, New York, 1966.
2.
StefanidisD., and JencksW. P., J. Am. Chem. Soc., 1993, 115, 6045.
3.
OakenfullD.G., RileyT., and GoldV., Chem. Commun., 1966, 385.
4.
OakenfullD.G., RileyT., and GoldV., J. Chem Soc. (B), 1968, 515.
5.
JohnsonS.L., Adv. Phys. Org. Chem., 1967, 5, 237.
6.
ButlerA.R., and RobertsonI. H., J. Chem., Perkin Trans.1975, 2, 660.
7.
BruiceP.Y., and BruiceT. C., J. Am. Chem. Soc., 1974, 96, 5523.
8.
JencksW.P., and GilchristM., J. Am. Chem. Soc., 1968, 90, 2622.
9.
SatterthwaitA.C., and JencksW. P., J. Am. Chem. Soc., 1974, 96, 7018.
10.
NeunovenH., JCS, Perkin Trans, 1987, 159.
11.
MaskillH., The Physical Basis of Organic Chemistry, Oxford Science Publications, New York, 1990.
