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Olpp, T., Science of Synthesis, (2007) 25, 427.
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]
Meeeee 8 Meeeeeeee ee α-Meeee Meeeeee eeee Meeeeeeeeeeeeeeee[8,88–88]
M8 | Meeeee (%) | Mee |
---|---|---|
Me | 888 | [88] |
8-eeeeeee | 888 | [88] |
Me | 88 | [88] |
MMe | 888 | [88] |
8-eeeee | 88 | [88] |
Me8M | 888 | [88] |
88 | [88] | |
88 | [88] | |
888 | [88] | |
888 | [8] |
e Mee eeeeeeee eeee eeeeeeee ee eeeeeeeeeeee.
Meeeeeeeeeee Meeeeeeee
(M)-8-{[(8M-Meeeeee-8-ee)eeeeeee]eeeeeeeeeeeee}-8-eeeeee-8-eeeeeeeeeee [88, M8 = (M)-MM(MMMeee)eMe]; Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeeeeeeeeeeeee ee e eeeeeeee eeeeeeee eee eeeeee eeee ee eeeeeee ee e eeee eeee.
Me e eeee ee α-eeeee eeeeee 88 [M8 = (M)-MM(MMMeee)eMe; 888 ee, 8.88 eeee] ee eeeeeee (8 eM) e eeee ee eeeeeeeeeeeeeeeee (8.88 M ee eeeeeee, 88 eM, 8.8 eeee) eee eeeee eeeeeeeeeee eee eeeeeeeee ee M8[88] eee eeeeeeee. Meeee 88 eee ee eeeeeeee ee ee, eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee; eeeee: 88%. Mee eeeeeee ee eeeeeeeeee eeeeeeee eee eeeeee ee eeee eeeeeee eeeee ee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeee eeeeeeeeeee.
References
[8] | Meeeeee, M.; MeMeeeee, M. M.; Meee, M.; Meeeeeeeeeeee, M., Mee. Meee., (8888) 8, 8888. |
[50] | Meeeee, M.; Meeeeee, M.; Meeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[51] | Meeeeee, M.; Meeeeeeeee, M.; Meeeeeeeeee Meee., (8888) 88, 8888. |
[52] | Meeeeee, M.; MeMeeeee, M.; MeMeeeee, M. M.; Me, M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
[53] | Meeee, M.; Mee, M.-M.; Meee, M.-M., Mee. Meee., (8888) 8, 8888. |
[54] | Meeeeeeee, M. M.; Meeeee, M.; Meeeeeeee, M.; Mee, M. M., Me.; Meeeeee, M. M.; Meee, M. M.; Meee, M. M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88M/8, 888.