Premium
The syntheses of ethoxycarbonyl‐1,3‐dioxoles and oxazoles from the copper catalyzed thermolysis of ethyl diazopyruvate in the presence of ketones, aldehydes and nitriles
Author(s) -
Alonso Miguel E.,
Jano Patricia
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170419
Subject(s) - chemistry , yield (engineering) , enol , catalysis , cycloaddition , thermal decomposition , copper , ethyl diazoacetate , carbene , organic chemistry , heteroatom , medicinal chemistry , salt (chemistry) , carbon fibers , ring (chemistry) , cyclopropanation , materials science , metallurgy , composite number , composite material
The copper salt‐catalyzed interaction of ethyl diazopyruvate with ketones, aldehydes and nitriles was examined. A variety of 1,3‐dioxoles and oxazoles was obtained in moderate yield. The formation of enol ethers, epoxides, carbon‐carbon insertion products, aziridines, and azetidines, typical products of carbene reactions with carbon‐heteroatom multiple bonds, was not observed. Evidence for the operation of a 1,3‐dipolar cycloaddition reaction is presented.