Abstract
Two new mild oxidizing agents 1,1,3,3-tetramethylguanidinium fluorochromate (TMGFC) and 1,1,3,3-tetramethylguanidinium chlorochromate (TMGCC) were prepared in high yields by reacting tetramethylguanidine with CrO3and related acid. These reagents are suitable to oxidize various primary and secondary alcohols and oximes to the corresponding carbonyl compounds under solvent-free conditions and microwave irradiation.
Highlights
Oxidation of various organic compounds under mild conditions is of great importance in synthetic organic chemistry [1]
In continuation of our ongoing research program for developing newer chromium reagents [25,26,27,28], two new oxidizing agents such as 1,1,3,3-tetramethylguanidinium fluorochromate (TMGFC) and 1,1,3,3-tetramethylguanidinium chlorochromate (TMGCC) shown in Figure 1 were synthesized with the belief that these reagents could be used for the oxidation of organic substrates
The higher pH values of TMGFC and TMGCC compared to their companion reagents attest to their far less pronounced acidic characters
Summary
Oxidation of various organic compounds under mild conditions is of great importance in synthetic organic chemistry [1]. Since the appearance of Collins reagent [2], significant improvements are achieved in the development of new Cr(VI) based oxidizing agents for the effective and selective oxidation of organic substrates, in particular alcohols, under mild conditions. The chromium based reagents that have been developed so far have some limitations that cannot be overlooked. These include the inherent problems of acidity of the reagents, instability, tedious work-up, a long reaction time, overoxidation, use of toxic solvent, or a need for excess amount of reagent [11,12,13,14,15,16,17,18]. In continuation of our ongoing research program for developing newer chromium reagents [25,26,27,28], two new oxidizing agents such as 1,1,3,3-tetramethylguanidinium fluorochromate (TMGFC) and 1,1,3,3-tetramethylguanidinium chlorochromate (TMGCC) shown in Figure 1 were synthesized with the belief that these reagents could be used for the oxidation of organic substrates
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