Electroorganic Chemistry. 81. Anodic Oxidation of Sulfonamides and Amidophosphates

Article abstract of DOI:10.1021/jo00194a008

Oxidation peak potentials of sulfonamides and amidophosphates were measured in acetonitrile and compared with the corresponding amides and carbamates.The results showed that the order of easiness of oxidation was amides > carbamates > amidophosphates > sulfonamides.Furthermore, the reaction of silyl enol ethers or trimethyl phosphite with anodically α-methoxylated sulfonamides or amidophosphates has clearly shown that the α-methoxylated compounds are useful starting materials in organic synthesis.For example, optically active L-tryptophan was synthesized from α-methoxylated N-(p-tolylsulfonyl)-L-proline ester.