Abstract
Few classical organic name reactions have been studied more extensively from a mechanistic and structural standpoint in recent years than the Claisen rearrangement. This reaction was discovered almost exactly fifty years ago by Ludwig Claisen (1) in his private laboratory at Godesberg on the Rhine shortly after his retirement from an extremely fruitful academic career (2). It consists of the thermally-induced isomerization af allyl ethers of enols and phenols to the corresponding C-allyl derivatives, e.g., allyl vinyl ether --> allylacetaldehyde, allyl phenyl ether -> o-allylphenol, etc. (3). From kinetic, product, and other data (3,4), it has been amply demonstrated that such rearrangements proceed intramolecularly, through a cyclic, quasi-six-membered ring transition state, which for allyl vinyl ether may be depicted:
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