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Synthesis 2016; 48(05): 772-782
DOI: 10.1055/s-0035-1561283
DOI: 10.1055/s-0035-1561283
paper
Geminal Dichlorination of Phenyliodonium Ylides of β-Dicarbonyl Compounds through Double Ligand Transfer from (Dichloroiodo)benzene
Further Information
Publication History
Received: 03 November 2015
Accepted after revision: 18 November 2015
Publication Date:
29 December 2015 (online)
Abstract
Pre-formed phenyliodonium ylides of cyclic and acyclic β-diketones, β-keto esters and β-diesters were reacted with (dichloroiodo)benzene, resulting in transfer of both chloride ligands onto the ylidic carbon. These two hypervalent iodine(III) compounds exhibit high reactivity towards each other under mild reaction conditions and typically afford the gem-dichloride products in good yield. Upon comparison of these chlorination reactions with those of the analogous diazocarbonyl compounds, reactions of iodonium ylides were unilaterally faster, and often gave the products in higher yield.
Key words
halogenation - hypervalent iodine - iodonium ylides - diazo compounds - (dichloroiodo)benzeneSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561283.
- Supporting Information
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For examples of other methods of transferring both halide ligands of (dihaloiodo)arenes in a geminal fashion, see:
The increased reactivity of iodonium ylides occasionally resulted in decreased product yields. A solution to this might be the use of stabilised aryliodonium ylides reported by Zhdankin. For examples, see: