Issue 0, 1983

Reaction of strained polycyclic ketones with diazomethane

Abstract

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1983, 1791-1797

Reaction of strained polycyclic ketones with diazomethane

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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