Abstract
An equatorial attack of TMS-diazomethane was determined to be the first step of the BF(3)-promoted ring expansion reaction of six-membered ketones using TMS-diazomethane. The migration reaction occurred in a conformation in which the carbonyl oxygen and the TMS group were antiperiplanar to predominantly afford trans-seven-membered ketones.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Diazomethane / analogs & derivatives*
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Diazomethane / chemical synthesis
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Diazomethane / chemistry*
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Ketones / chemical synthesis*
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Ketones / chemistry
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Molecular Structure
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Stereoisomerism
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Trimethylsilyl Compounds / chemical synthesis
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Trimethylsilyl Compounds / chemistry*
Substances
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Ketones
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Trimethylsilyl Compounds
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Diazomethane
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trimethylsilyldiazomethane