Chemistry of novel compounds with multifunctional carbon structure. Part 3. Synthesis of α-azido-α-fluoro-α-(phenylthio and ethylthio)acetates

Abstract

The synthesis of tri- and tetra-functional carbon compounds which possess three or four different functional groups on the same carbon atom is described.Reactions of ethyl bromofluoro- or chlorofluoro-acetate (4b) or (5) with several heteroatomic nucleophiles give the corresponding α-functionalised α-fluoroacetates (6a–g) in good yields. The trifunctional carbon compounds which have phenylthio and ethylthio functionalities (6a,b) are brominated with NBS to afford the tetrafunctional carbon compounds, ethyl bromofluoro(phenylthio and ethylthio)acetates (8a,b). The bromo derivatives (8a,b) can be converted into another type of tetrafunctional carbon compound, ethyl azidofluoro(phenylthio and ethylthio)acetates (9a,b) by reaction with sodium azide under phase-transfer conditions. Ethyl azidobromofluoroacetate (12) is prepared from the dibromo derivative (4c) in a similar manner.The noticeable reactivities which are caused by the novel multifunctionalised carbon structures are also reported.