Synthesis and Use of α-Diazo Oxime Ethers in the Synthesis of Ethylene Diketone Bis(O-methyloxime) Derivatives

Abstract

Reaction of the lithium salts of oxime ethers 4a–c with methanesulfonyl azide gives the α-diazo oxime ethers 5a–c. These novel compounds are stable up to 90°C, however, they decompose thermally in refluxing CCl4 and with PdCl2 catalysis to yield the ethylene diketone bis(O-methoxyloxime) derivatives 6a–c in yields of 85–91%. The preparation and characteristic spectral features of 5a–c are described.