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Magnesium bis(monoperoxyphthalate) hexahydrate

Chemfiles Volume 5 Article 1

Magnesium bis(monoperoxy- phthalate) hexahydrate (mono peroxyphthalic acid magnesium salt, or MMPP) is a mild, general oxidizing agent which is a suitable replacement for peroxycarboxylic acids. This versatile reagent is capable of effecting many types of general oxidation reactions.1 In addition, MMPP displays low toxicity, and is safer to use in larger-scale reactions, compared to common peroxycarboxylic acids. The reaction by-product, magnesium bisphthalate, is water soluble, and generally easy to separate during work-up.

Recently, the difficult oxidation of glycosyl sulfides to the sulfoxide has been achieved using moist MMPP and microwave irradiation (MW) (Scheme 32). The yields using MMPP were superior to those achieved using other oxidants such as oxone or sodium periodate, and no over-oxidation to the sulfone was observed.2

Scheme 32

MMPP was also used in the formation of a unique alkenyl tricarbonyl, which was used as a common precursor in the synthesis of a series of heterocyclic substituted amino acids (Scheme 33).3

Scheme 33

MMPP was used in conjunction with ultrasound stimulation to produce 2-aryl-3-hydroxysultams and 2-aryl-3-alkoxysultams in one step from the isothiazolium salt (Scheme 34).4

Scheme 34

Whereas most aromatic aldehydes are oxidized to the correspond-ing carboxylic acids, it has been reported that o- and p-methoxy-benzaldehydes can be converted to the analogous phenols in pres- ence of MMPP (Scheme 35).5

Scheme 35

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References

  1. Brougham, P. et al Synthesis 1987, 1015.
  2. Chen, M-Y. et al. J. Org. Chem. 2004, 69, 2884.
  3. Wasserman, H. H. et al. Tetrahedron Lett. 2002, 43, 3351.
  4. Taubert, K. et al. Synthesis 2003, 2265.
  5. Heaney, H. and Newbold, A. J. Tetrahedron Lett. 2001, 42, 6607.

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