Aryne chemistry. Part XIX. Some reactions of tetrachloro-4-methoxypyridine with Grignard reagents and organolithium compounds

Abstract

Sterically non-demanding Grignard and organolithium reagents displace the methoxy-group in tetrachloro-4-methoxy-pyridine, with the formation of 4-alkyl- or 4-aryl-tetrachloropyridines. t-Butyl-lithium forms trichloro-4-methoxy-3-pyridyl-lithium, which decomposes in the presence of furan with the formation of 2,3-dichloro-5,8-dihydro-4-methoxy-5,8-epoxyquinoline.