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25.2.1.1.7 Method 7: Cleavage of C=C Bonds

DOI: 10.1055/sos-SD-025-00278

Olpp, T.Science of Synthesis, (200725430.

The ozonolysis of unsaturated carbonyl compounds to deliver glyoxals has been reported (Scheme 10).[‌72‌‌75‌] Enones 26 and 28 give 1 equivalent of glyoxals 27 and 29, respectively, and 1 equivalent of benzaldehyde as a byproduct (for 26, 96% of product 27 is obtained as the monohydrate and for 28, 80% as the monohydrate of glyoxal 29). Even arenes undergo oxidative cleavage: glyoxal (30) is obtained from the ozonolysis of naphthalene in 66% yield as osazone, with 68% of phthalaldehyde (31) as byproduct. 1,3-Dienes are also shown to give glyoxals upon ozonolysis (methylglyoxal from isoprene).[‌76‌] A variation is the oxidative cleavage of the C=P bond of acylphosphoranes by sodium periodate.[‌77‌]

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