Tetrahedron Letters p. 5625 - 5628 (1994)
Update date:2022-07-29
Topics:
Adam, Waldemar
Hadjiarapoglou, Lazaros
Mielke, Karsten
Treiber, Alexander
In addition to the expected dimethyldioxirane (DMD) oxidation of diazoquinones 1 to their quinones 2, the corresponding epoxy quinones 3 are formed directly and not as secondary overoxidation products of the quinones 2 since the latter are persistent towards DMD under these conditions; this novel oxidation is rationalized in terms of the ambident nucleophilic nature of the diazoquinones and corroborated by MO (AMI) calculations.
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