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25.2.1.1.3 Method 3: Oxidation of α-Diazo Ketones

DOI: 10.1055/sos-SD-025-00278

Olpp, T.Science of Synthesis, (200725427.

The oxidation of α-diazo ketones 14 with dimethyldioxirane (DMDO) represents an efficient and general preparation of glyoxals 15 (Scheme 5).[‌50‌] The products are obtained in high yields and high purity without purification because the only byproducts are nitrogen and acetone. Furthermore, this method tolerates stereocenters α to the glyoxal oxo group[‌51‌,‌52‌] as well as epoxides[‌8‌] and azides.[‌53‌] A variation of this transformation is reported, in which an α-diazoketone 14 is treated successively with triphenylphosphine (to give a phosphazine, R1COCH=NN=PPh3) and nitrous acid to produce glyoxal 15.[‌54‌]

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References


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