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.