Base-catalyzed deuterium and tritium labelling of 1-biphenyl-4-ylpropane-1,2-dione and deuteration of aryl methyl ketones

A synthesis and a base-catalyzed exchange reaction was developed under mild conditions to deuterate and subsequently tritiate the methyl group of the base sensitive diketone 1-biphenyl-4-ylpropane-1,2-dione depicted in Figure 1. Using Et3N as base, deuterium incorporation of the methyl group was 88.9% and the tritium incorporation gave a specific radioactivity of 119 mCi/mmol. The scope of the exchanges was extended to methyl aryl ketones 2-4. Copyright (C) 2004 John Wiley Sons, Ltd.