Stable Five-Membered Cyclic Alkynes
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- Suzuki Noriyuki
- Chemical Analysis Team, RIKEN
Bibliographic Information
- Other Title
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- 安定に単離できる5員環アルキン化合物
- アンテイ ニ タンリデキル 5インカン アルキン カゴウブツ
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Abstract
It is generally known that small cyclic alkynes such as cyclopentyne is extremely reactive and unstable. Therefore it has been believed impossible to isolate cyclopentyne compounds.<BR>We recently reported that low-valent group 4 metallocenes reacted with 1, 2, 3-butatrienes to give 1-metallacyclopent-3-yne complexes and that resulted compounds are surprisingly stable and isolable. We succeeded in determination of their molecular structures by X-ray diffraction analyses, and showed that these are five-membered cyclic alkynes, while π, π-interaction of butatriene was also suggested. In this review, the preparation, structure and reactivity of these 1-metallacyclopent-3-yne compounds are described.<BR>The 1-zirconacyclopent-3-yne complexes reacted with another 'zirconocene' to form bimetallic complexes in which the cyclic alkyne coordinated to the other zirconocene moiety, indicating that the zirconacyclopentyne behaved as an alkyne. Seven-membered cyclic alkynes were also prepared from 1, 2, 3-butatriene and a zirconocene-alkyne compound. Protonolysis and subsequent nucleophilic attack to aldehyde gave allenyl or dienyl alcohol depending on proton source.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 65 (4), 347-357, 2007
The Society of Synthetic Organic Chemistry, Japan
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Details 詳細情報について
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- CRID
- 1390282680289342464
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- NII Article ID
- 10018898823
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- NII Book ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BD2sXktlCiur8%3D
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 8788689
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed