Journal of the American Chemical Society

The Steric Course of the Claisen Rearrangement

AW Burgstahler

Index: Burgstahler,A.W. Journal of the American Chemical Society, 1960 , vol. 82, p. 4681 - 4685

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Citation Number: 23

Abstract

An infrared study of the stereochemistry attending the Claisen rearrangement of cis-and trans-@, ydimethylallyl and two other related vinyl ethers has shown that the reaction produces essentially only trans substituted allylacetaldehydes. The double bond in the o- Claisen rearrangement product of trans-c~, r-dimethylallyl phenyl ether has also been demonstrated by infrared absorption to be predominantly trans. The transition state ...