Bicyclo[3.3.1]nonane and its derivatives—IV : Reactions of some carbonyl derivatives of bicyclo[3.3.1]nonane with diazomethane

Add time:09/02/2019    Source:sciencedirect.com

The reaction of bicyclo[3.3.1]nonane-2,6-dione with diazomethane in situ does not lead to the homologous bicyclo[4.3.1]decane-2,7-dione, but mainly to tricyclo[4.4.0.02,9]decan-9-ol-5-one. The structure of the latter was confirmed by the proton NMR spectra measured with an addition of Eu(DPM)3, A mixture of tricyclo[4,4.0.02,9]decan-9-ol-5-one and bicyclo[4.3.1]decane-2,7-dione results when solutions of diazomethane are used. The reaction of bicyclo[3.3.1]nonane-2,6-dione monoethyleneacetal with diazomethane in situ yields predominantly bicyclo[4.3.1]decane-2,7-dione. Under the same conditions bicyclo[3.3.1]nonan-2-one gives with diazomethane in situ only bicyclo[4.3.1]decan-2-one.

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