2000年9月
Acid-catalyzed rearrangement of ethynylcycloheptatriene to phenylallene
ORGANIC LETTERS
- ,
- ,
- ,
- 巻
- 2
- 号
- 19
- 開始ページ
- 3011
- 終了ページ
- 3013
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1021/ol006328e
- 出版者・発行元
- AMER CHEMICAL SOC
GRAPHICS
7-Ethynylcycloheptatriene (1) cleanly isomerizes to phenylallene in the presence of acid. A mechanism involving the protonation of ethynylnorcaradiene, which is in equilibrium with 1, followed by the cleavage of a three-membered ring to give an arenium ion, is proposed. The rearrangement is accelerated by a factor of 370 by introducing tert-butyl groups on C-2 and C-5, indicating the importance of the equilibrium concentration of the norcaradiene form as a rate-controlling factor.
7-Ethynylcycloheptatriene (1) cleanly isomerizes to phenylallene in the presence of acid. A mechanism involving the protonation of ethynylnorcaradiene, which is in equilibrium with 1, followed by the cleavage of a three-membered ring to give an arenium ion, is proposed. The rearrangement is accelerated by a factor of 370 by introducing tert-butyl groups on C-2 and C-5, indicating the importance of the equilibrium concentration of the norcaradiene form as a rate-controlling factor.
- リンク情報
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- DOI
- https://doi.org/10.1021/ol006328e
- CiNii Articles
- http://ci.nii.ac.jp/naid/80012074745
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/10986095
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000089386100024&DestApp=WOS_CPL
- ID情報
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- DOI : 10.1021/ol006328e
- ISSN : 1523-7060
- CiNii Articles ID : 80012074745
- PubMed ID : 10986095
- Web of Science ID : WOS:000089386100024