TRANSAMINATION STUDIES ON N-(1-ALKENYLTHIO)PHTHALIMIDES AND RELATED-COMPOUNDS - SYNTHESIS OF 1-ALKENESULFENAMIDES AND 1-ALKENESULFONAMIDES

In an attempt to develop a method for the general preparation of 1-alk enesulfenamides, some N,N-bis(trimethylsilyl)-1-alkenesulfenamides (4) were converted to a number of nitrogen functionalized analogs through desilylation and acylation procedures. Mono- and dibenzoylated deriva tives 5a and 6a did not undergo transamination reactions with simple a mines. Transamination reactions could be achieved once compounds 4 wer e converted to thiophthalimides 7. The transamination products 8 are u nstable to chromatography, but could be oxidized to 1-alkenesulfonamid es 9 using MCPBA. Some of the sulfenamides 8 may be stable to distilla tion. 3-(Alkenylthioimino)phthalides 11, isomers of thiophthalimides 7 , also react with amines, but the process of ring opening accompanies transamination. It was found that the transamination reactions of 11 p robably involve the intermediacy of isomers 7.