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Synlett 2005(11): 1807-1808  
DOI: 10.1055/s-2005-871570
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Magnesium Bis(monoperoxyphthalate) Hexahydrate (MMPP)

Manuel Alcarazo Velasco*
Instituto de Investigaciones Químicas (CSIC-USe), Américo Vespucio s/n, 41092-Sevilla, Spain
e-Mail: malcarazo@iiq.csic.es;
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Publikationsdatum:
28. Juni 2005 (online)

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Introduction

Magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) is a commercially available, inexpensive, and relatively stable reagent suitable for the oxidation of a ­variety of organic substrates. It is easy and safe to handle, even in large-scale reactions. MMPP has been used for the oxidation under mild conditions of a wide range of compounds including alkenes, ketones, sulfides, sulfoxides, hydrazones and hydrazides, and is thus one of the most ­attractive peroxyacids for this type of reaction.

Besides stability and safety advantages, there are additional practical aspects to this reagent: (1) since it is water-soluble, excess MMPP or the resulting magnesium bis(phthalate) can be removed from the reaction mixture by a simple aqueous work-up; and (2) it can be used in buffered solutions, thus the range of functional groups that ­tolerates the reaction conditions is increased.

The most evident disadvantage of the reagent is also related to its solubility: since it is a salt, it has low solubility in the most common non-polar solvents. Recently, however, the use of a solid-phase-supported version of the reagent on silica gel has been successfully applied to overcome this limitation in some particular cases. [1]