書誌事項
- タイトル別名
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- Selective transformations of functional groups by use of dialkyl phosphonates.
- ホスホンサン ジアルキル オ モチイル センタクテキ カンノウキ ヘンカン
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Dialkyl phosphonate works as a reducing agent in the presence of triethylamine towards gem-dibromocyclopropanes and gem-dibromoolefins to give the corresponding monobromo derivatives, respectively. Reduction of gem-bromochlorocyclopropanes, 1, 1, 1-trichloromethane derivatives, 1, 1-dibromo-2-benzyloxyethylene, methyl α-bromocinnamate, α, p-dibromoacetophenone, and (1, 2-dibromoethyl) benzene is surveyed. Treatment of α-bromo- α, β-unsaturated carbonyl compounds or 1, 1-dibromo-2-trimethylsiloxycyclopropanes with dialkyl phosphonate and triethylamine affords, β, γ-unsaturated carbonyl compounds stereoselectively. This reductive deconjugation is applied to the syntheses of naturally occurring compounds, recifeiolide and pyrenophorin. Reductive phoshonation of gem-dibromocyclopropanes is performed by treatment with trialkyl phosphite-dialkyl phosphonate-triethylamine or trialkyl phosphite-triethylamine-water resulting in the formation of dialkyl cyclopropylphosphonates. The palladium-catalyzed reactions of aryl bromides or iodides with dialkyl phosphonates in the presence of triethylamine give the corresponding arylphosphonates. This method is extended to the stereospecific phosphonation of vinyl bromides.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 45 (8), 784-791, 1987
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390282680287522560
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- NII論文ID
- 130000931157
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 3144188
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
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