BASIC MEDIA BEHAVIOR OF N- ETHYL CARBAMATES (Y=SMe, SOMe, SO2Me, H, Br, CN)

Article abstract of DOI:10.1016/0040-4020(89)80047-X

From the results obtained in the hydrolysis reaction of the carbamate group of some thioderivatives compounds whose common structure is (2-EtOOCNH-C6H4)-CHOH-CH2Y a mechanism is suggested to explain the products, as well as the relationship between the relative configuration of diastereoisomeric sulfoxides (Y=SOMe) with the reaction rate and with the stereochemical outcome.Other interesting and unexpected products are yielded when the hydrolysis reaction of other carbamates (Y=H, Br, CN) is carried out.In the present cases, the carbamate function seems to behave as a very versatile group capable of readily undergoing conversions to several kinds of heterocycles.