Abstract
The synthesis and rhodium mediated O-H insertion reactions of a wide range of diazo compounds are described. The rate at which the diazo compounds decompose in the presence of 2-propanol and the rhodium catalyst is strongly dependent on the electron withdrawing group(s) attached to the diazo carbon, with diazophosphonates being the least reactive. Insertion into the O-H bond of methanol, t-butanol and phenols was also investigated, as well as the effect of catalyst. In some cases ‘reduction’ of the diazo group to the corresponding CH 2 group competes with O-H insertion, although this is highly catalyst and substrate dependent. Of the catalysts used, rhodium(II) trifluoroacetamide is the most effective for O-H insertion reactions.
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