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Synthesis 2012; 44(14): 2155-2161
DOI: 10.1055/s-0031-1290776
DOI: 10.1055/s-0031-1290776
special topic
Lewis Acid Promoted Reactions of 1,1-Diarylallenes and Ketone Derivatives: Synthesis of Indenes by an Addition/Cyclization Reaction
Further Information
Publication History
Received: 19 December 2011
Accepted: 01 March 2012
Publication Date:
03 April 2012 (online)
Abstract
The Lewis acid promoted reaction of 1,1-diarylallenes with ketone derivatives was examined. The tin(IV) chloride promoted reaction of diarylallenes with vinyl ketones gave indene derivatives through a conjugate addition/cyclization reaction. The reaction of diphenylallene with diethyl oxomalonate in the presence of one equivalent of tin(IV) chloride at –40 °C gave diethyl hydroxy(3-phenyl-1H-inden-2-yl)malonate as the major product through a carbonyl addition/cyclization reaction, whereas the same reactants in the presence of 0.2 equivalents of tin(IV) chloride at 80 °C gave diethyl (3-phenyl-1H-inden-2-yl)malonate. Diethyl hydroxy(3-phenyl-1H-inden-2-yl)malonate was also converted into the latter product on heating at 80 °C in the presence of 0.2 equivalents of tin(IV) chloride.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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