Cyclohexenyl esters

Fig. 6.14. Possible transition structures for [3,3]-sigmatropic rearrangement of 2-cyclohexenyl ester enol ethers. Adapted from J. Org. Chem., 68, 572 (2003), by permission of the American Chemical Society.

Acetic acid, butyl ester Acetic acid, pentyl ester Acetic acid, decyl ester Acetic acid, benzyl ester Acetic acid, benzyl ester Acetic acid, 1-cyclohexenyl ester Acetic acid, 3-cyclohexenyl ester Butyric acid, benzyl ester Phenylacetic acid, propyl ester Oleic acid, methyl ester Linoleic acid, methyl ester Linolenic acid, methyl ester Adipic acid, methyl ester Adipic acid, ethyl ester Adipic acid, diethyl ester Adipic acid, dipropyl ester Adipic acid, (methylethyl)ester Adipic acid,... 

In a related system, Feringa and co-workers (104) noted the beneficial effect of copper bronze in the allylic oxidation reaction. The addition of 5 mol% of this addend provides the cyclohexenyl ester in higher selectivity and yield than in the absence of the metal, while allowing the reaction to proceed at 0°C. The role of copper bronze is presumably to effect reduction of Cu(II) to the catalytically active... 

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