書誌事項
- タイトル別名
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- The Problem of Non-Recognition for Dienes in Ketene Reactions
- ケテン ノ ジエン フ ニンシキ モンダイ ケテン カガク ニ オケル オオキ
- A Big Fault in Ketene History and Its Solution
- ケテン化学における大きな誤謬とその解答
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説明
Non-recognition for dienes in ketene reactions has long been an important problem in organic chemistry since the diphenylketene-cyclopentadiene reaction was found by Staudinger in 1920. Recently, we have discovered that the ketene recognizes conjugated dienes. The ketene is a dienophile not for well-known [2+2] cycloadditions but for [4+2] (Diels-Alder) reactions across its C=O bond. This paper outlines the long history of ketene chemistry and describes the way of how the problem has been tackled. The frontier-orbital theory and ab initio calculations have predicted that ketene should react with cyclopentadiene via the [4+2] cycloaddition and a subsequent Claisen rearrangement. Careful low-temperature experiments and NMR spectroscopy of the reaction have demonstrated the first detection of the [4+2] -type cycloadduct and the conversion to the final product, cyclobutanone, by the rearrangement.
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 55 (1), 56-64, 1997
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
- 1390282680287464576
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- NII論文ID
- 10009335305
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 4129276
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