Tetrahedron letters

Competitive epoxidation and quinone formation in the dimethyldioxirane oxidation of diazoquinones as ambident nucleophiles

W Adam, L Hadjiarapoglou, K Mielke, A Treiber

文献索引：Adam, Waldemar; Hadjiarapoglou, Lazaros; Mielke, Karsten; Treiber, Alexander Tetrahedron Letters, 1994 , vol. 35, # 31 p. 5625 - 5628

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被引用次数: 7

摘要

Abstract 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 (AM1) calculations.