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1.
Chem Commun (Camb) ; 49(44): 5010-2, 2013 Jun 04.
Article in English | MEDLINE | ID: mdl-23620239

ABSTRACT

Three new fumaramide-derived [3]rotaxanes have been synthesized, with the aim of macrocycle linking to form a molecular box. In one case, a nine-component templated [3]rotaxane synthesis was accomplished in 40% yield. Rotaxane reduction resulted in an unexpectedly facile de-slipping process.

2.
Chem Soc Rev ; 38(11): 3082-91, 2009 Nov.
Article in English | MEDLINE | ID: mdl-19847343

ABSTRACT

This tutorial review covers the applications of aromatic compounds such as anisole derivatives as synthetic equivalents (synthons) for 1,3-dicarbonyl compounds. The aromatic nucleus is first converted under reductive Birch conditions to the corresponding 1,4-cyclohexadiene compound which is then subjected to ozonolysis. The reductive work-up of the ozonides generates the 1,3-dicarbonyl compounds. The usefulness of this reaction sequence is demonstrated in several syntheses of complex molecules. A new access to 1,3-dicarbonyl compounds by an alternative approach utilising a cobalt-catalysed Diels-Alder reaction or a 1,4-hydrovinylation reaction to generate the needed 1,4-diene derivatives is briefly discussed.

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