THE LEAD-TETRAACETATE OXIDATION OF BISACYLHYDRAZONES OF ALPHA-DIKETONES - A SCOPE REASSESSMENT

Authors
MAROULIS AJ AKRIVOS PD HADJIANTONIOUMAROULIS CP
Citation
Aj. Maroulis et al., THE LEAD-TETRAACETATE OXIDATION OF BISACYLHYDRAZONES OF ALPHA-DIKETONES - A SCOPE REASSESSMENT, Journal of heterocyclic chemistry, 30(4), 1993, pp. 913-916
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
30
Issue
4
Year of publication
1993
Pages
913 - 916
Database
ISI
SICI code
0022-152X(1993)30:4<913:TLOOBO>2.0.ZU;2-Z
Abstract
Oxidation of the title compounds yields, besides the reported isoimide s 3 and/or the amides 4, also the imides 5. The observed product dicho tomy is considered as the result of an intramolecular nucleophilic att ack on the aroyl group, of the pressumed zwitterionic intermediate 2, by O or N present in the ambident N-aroylimine site of 2. The results of AM1 calculations agree with the product studies and both permit the formulation of a set of rules correlating structure and selectivity.