Hypoiodous acid initiated rearrangement of tertiary propargylic alcohols to α-iodoenones
نویسندگان
چکیده
منابع مشابه
Hypoiodous acid initiated rearrangement of tertiary propargylic alcohols to α-iodoenones.
In the presence of an oxidant, sodium iodide is converted into hypoiodous acid which effects the rearrangement of tertiary propargylic alcohols to α-iodoenones in good yields.
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[formula: see text] Treatment of tertiary propargylic alcohols 13 with 3-diazo-2-butanone 6 and catalytic dirhodium tetraacetate in benzene gave good yields of the diastereomeric allenic hydroxyketones 14, with, in some cases, good diastereocontrol. These products are presumably formed via the [2,3]-sigmatropic rearrangement of an alpha-propargyloxy enol derivative. This reaction has been exten...
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The regioselective gold-catalysed hydration of propargylic alcohols to β-hydroxy ketones can be achieved by diverting the gold-catalysed Meyer-Schuster rearrangement through the addition of a protic additive with a pKa of 7-9 such as p-nitrophenol, boric acid or a boronic acid. This provides an interesting alternative to an aldol reaction when combined with the straightforward addition of an al...
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ژورنال
عنوان ژورنال: Organic & Biomolecular Chemistry
سال: 2012
ISSN: 1477-0520,1477-0539
DOI: 10.1039/c2ob26360b