ChemInform Abstract: STERIC EFFECTS ON THE TITANIUM TETRACHLORIDE PROMOTED DIMERIZATION OF SILYL KETENE ACETALS

To generalize oxidative radical cyclizations of malonate enolates induced by recyclable single electron transfer (SET) oxidant ferrocenium hexafluorophosphate 1, the reactivity of a series of enolates 3 that differ only in their counterions was studied. Only lithium enolates were oxidized by 1, irrespective of their generation method. The presence of amines in stoichiometric or substoichiometric amounts is necessary for SET oxidation-bicyclization of Na, K, Mg, Zn, Si, or Ti enolates 3. The nucleophilicity of 3, the amine, and the presence of halide ions determine the bicyclization yield of lactone 7.

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Oxidative radical cyclizations of malonate enolates induced by the ferrocenium ion – a remarkable influence of enolate counterion and additives

Jahn

Hartmann

2001

J. Chem. Soc., Perkin Trans. 1

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ChemInform Abstract: STERIC EFFECTS ON THE TITANIUM TETRACHLORIDE PROMOTED DIMERIZATION OF SILYL KETENE ACETALS

Abstract: Die TiCh‐katalysierte Dimerisierung der Silylketenacetale (I) zum Dicarbonsäureester (II) wird untersucht.

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Oxidative radical cyclizations of malonate enolates induced by the ferrocenium ion – a remarkable influence of enolate counterion and additives

Oxidative radical cyclizations of malonate enolates induced by the ferrocenium ion – a remarkable influence of enolate counterion and additives

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