Arylation of diethyl alkylmalonates: synthetic route to diethyl alkyl(substituted aryl)malonates with the aid of temporary arene complexation by the cyclopentadienyliron moiety

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dc.creator Piorko, Adam
dc.creator Abd-El-Aziz, Alaa S.
dc.creator Lee, Choi Chuck
dc.creator Sutherland, Ronald G.
dc.date.accessioned 2013-05-29T18:36:07Z
dc.date.available 2013-05-29T18:36:07Z
dc.date.issued 1989
dc.identifier.issn 0300-922X
dc.identifier.uri http://library2.smu.ca/xmlui/handle/01/24975
dc.description Publisher's version/PDF
dc.description.abstract Nucleophilic substitution of chlorine in the ironcyclopentadienyl hexafluorophosphates of chlorobenzene, isomeric chlorotoluenes and dichlorobenzenes (1 ) with the anions generated from diethyl alkylmalonates (2) and (3) leads to the formation of ironcyclopentadienyl complexes of diethyl alkyl(substituted pheny1)malonates (4) and (5). An excess of the anion employed in reactions with the m- and p-dichlorobenzene complexes leads to substitution of both chlorine atoms and formation of isomeric phenylenedimalonate complexes (8). Malonyl cations (4) and (5) possessing a chloro substituent on the complexed phenyl ring provide the possibility of further modifications of phenyl ring substituents via substitution [complex (1 O)] or addition reactions [complexes (I 2)]. The described complexes have been demetallated giving diethyl alkyl(substituted pheny1)malonates in >50% overall yield from the cations (1). All the complexes and compounds have been fully characterized. This approach to the synthesis of the diethyl alkyl(substituted pheny1)malonates which are intermediates in the synthesis of important biologically active barbiturates is easy, efficient, and currently the most general in the area. en_CA
dc.language.iso en en_CA
dc.publisher Royal Society of Chemistry
dc.subject.lcsh Barbiturates -- Synthesis
dc.title Arylation of diethyl alkylmalonates: synthetic route to diethyl alkyl(substituted aryl)malonates with the aid of temporary arene complexation by the cyclopentadienyliron moiety en_CA
dc.type Text en_CA
dcterms.bibliographicCitation Journal of the Chemical Society, Perkin Transactions 1, 469-475. (1989)


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