Phase-transfer catalysis-3: Acetylation of 2-acylcycloalkanones |
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Authors: | R Alan Jones Malcolm J Stokes |
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Institution: | School of Chemical Sciences, University of East Anglia, NorwichNR4 7TJ England |
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Abstract: | With the exception of 2-formylcyclohexanone, which yields the E-exo-enol acetate, the phase-transfer catalysed acetylation of 2-acylcyclohexanones produces the 1-acetoxycyclohexene derivatives as the major products. The 1-acetoxy derivative is also obtained in good yield from the acetylation of 2-methoxycarbonylcyclopentanone but, generally, acetylation of 2-acylcyclopentanones yields the E-exo-enol acetates. 2-Acetylcyclopentanone, however, produces not only the E- and Z-exo-enol acetates, but also the endo-enol acetate, in a ratio of ca 2:2:1. The exo and endo-enol acetates were distinguished by 13CNMR spectroscopy and use of LIS reagents confirmed the configurational assignments of the exo-isomers |
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