The Effect of Metal Oxycarbonyl Group on the Claisen Rearrangement

Yutaka OKADA; Takashi UENO; Takatoshi HAYASHI

doi:10.5650/jos.52.491

Chemistry and Organic Synthesis

The Effect of Metal Oxycarbonyl Group on the Claisen Rearrangement

Yutaka OKADA, Takashi UENO, Takatoshi HAYASHI

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Keywords: Claisen rearrangement, substituent effect, alkali metal, alkaline-earth metal, chelate effect

JOURNAL FREE ACCESS

2003 Volume 52 Issue 9 Pages 491-493

DOI https://doi.org/10.5650/jos.52.491

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Abstract

The Claisen rearrangement of 2-allyloxybenzoic acid and its alkali and alkaline-earth metal salts was carried out. For the alkali metal salts, no accelerated effect was observed. There is also no accelerated effect for alkali metal salts in a nonpolar solvent. However, a significantly high reactivity was observed for the alkaline-earth metal salts in a nonpolar solvent. This is attributed to the chelate formation between the ethereal oxygen and the -COO^-.

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