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The lead tetraacetate oxidation of bisacylhydrazones of α‐diketones: A scope re‐assesment
Author(s) -
Maroulis A. J.,
Akrivos P. D.,
HadjiantoniouMaroulis C. P.
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300412
Subject(s) - chemistry , intramolecular force , nucleophile , scope (computer science) , selectivity , product (mathematics) , medicinal chemistry , group (periodic table) , organic chemistry , combinatorial chemistry , catalysis , geometry , mathematics , computer science , programming language
Oxidation of the title compounds yields, besides the reported isoimides 3 and/or the amides 4 , also the imides 5 . The observed product dichotomy is considered as the result of an intramolecular nucleophilic attack 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.