COMPETITIVE EPOXIDATION AND QUINONE FORMATION IN THE DIMETHYLDIOXIRANE OXIDATION OF DIAZOQUINONES AS AMBIDENT NUCLEOPHILES

Authors
ADAM W HADJIARAPOGLOU L MIELKE K TREIBER A
Citation
W. Adam et al., COMPETITIVE EPOXIDATION AND QUINONE FORMATION IN THE DIMETHYLDIOXIRANE OXIDATION OF DIAZOQUINONES AS AMBIDENT NUCLEOPHILES, Tetrahedron letters, 35(31), 1994, pp. 5625-5628
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
31
Year of publication
1994
Pages
5625 - 5628
Database
ISI
SICI code
0040-4039(1994)35:31<5625:CEAQFI>2.0.ZU;2-D
Abstract
In addition to the expected dimethyldioxirane (DMD) oxidation of diazo quinones 1 to their quinones 2, the corresponding epoxy quinones 3 are formed directly and not as secondary overoxidation products of the qu inones 2 since the latter are persistent rewards DMD under these condi tions; this novel oxidation is rationalized in terms of the ambident n ucleophilic native of the diazoquinones and corroborated by MO (AM1) c alculations.