The reaction of 1,4-bishomocubanone (1) with ethereal diazomethane leads to a mixture of the homologous ketone (2)(37%) and the aldol-type dimer (3)(32%). In the presence of methanol the reaction yields predominantly the ketone (2)(70%). Other constrained ketones are shown to react with diazomethane in an analogous way. The mechanism is discussed in terms of the influence of ring strain.
K. Hirao, Y. Kajikawa, E. Abe and O. Yonemitsu, J. Chem. Soc., Perkin Trans. 1, 1983, 1791 DOI: 10.1039/P19830001791
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