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Olpp, T., Science of Synthesis, (2007) 25, 430.
The ozonolysis of unsaturated carbonyl compounds to deliver glyoxals has been reported (Scheme 10).[72–75] 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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References
[72] | Meeee, M., Me Meeeee–Meee, (8888); Mee. 8/8, e 888. |
[73] | Meeeeeeeee, M.-M.; Meeeeeee, M., Me Meeeee–Meee, (8888); Mee. M 8, e 888. |
[74] | Meeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
[75] | Meeeeeee, M.; Meeeeeeee, M.; Meeeeeeee, M.; Meee, M. M.; Meeee, M.; Meeeeeeee, M. M., Meeeeeeeeee (8888) 88, 8888. |
[76] | Meeeeeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeee, M.-M.; Meeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 888. |
[77] | Meeeeeee, M.-M.; Meeeee, M.; Meeeee, M., Meee. Mee., (8888) 888, 8888. |
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- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 88.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.