The Journal of Organic Chemistry

Lanthanide-induced shift investigation of. alpha.-alkoxy aldehydes. A spectroscopic search for evidence of chelation in the Lewis acid catalyzed hetero-Diels-Alder …

MM Midland, RW Koops

Index: Midland, Mark M.; Koops, Roger W. Journal of Organic Chemistry, 1990 , vol. 55, # 15 p. 4647 - 4650

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Citation Number: 28

Abstract

Lanthanide-induced shift studies were performed using a chiral lanthanide shift reagent Eu (hfc),. Simple ethers exhibited little complexation to the shift reagent. Simple aldehydes produced large lanthanide-induced shifts. The a-alkoxy aldehydes gave lanthanide-induced shifts consistent with contributions from a" chelated" species. The degree of chelation was dependent on the steric bulk of the alkyl side chain.