Alternative General Synthetic Routes to [2.2]Cyclophanes and [3.2]Cyclophanes from [3.3]Cyclophane-2,11-diones by Photodecarbonylation, and a Structural Study of [3.2]Metacyclophanes
2001; Wiley; Volume: 2001; Issue: 13 Linguagem: Inglês
10.1002/1099-0690(200107)2001
ISSN1434-193X
AutoresH. Isaji, M. Yasutake, Hiroyuki Takemura, Katsuya Sako, Hitoshi Tatemitsu, Takahiko Inazu, Teruo Shinmyozu,
Tópico(s)Supramolecular Chemistry and Complexes
ResumoEuropean Journal of Organic ChemistryVolume 2001, Issue 13 p. 2487-2499 Full Paper Alternative General Synthetic Routes to [2.2]Cyclophanes and [3.2]Cyclophanes from [3.3]Cyclophane-2,11-diones by Photodecarbonylation, and a Structural Study of [3.2]Metacyclophanes Hajime Isaji, Hajime Isaji Institute for Fundamental Research of Organic Chemistry (IFOC), Kyushu University, Fukuoka 812-8581, Japan, Fax: (internat.) + 81-92/642-2735 Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka, 812-8581, JapanSearch for more papers by this authorMikio Yasutake, Mikio Yasutake Institute for Fundamental Research of Organic Chemistry (IFOC), Kyushu University, Fukuoka 812-8581, Japan, Fax: (internat.) + 81-92/642-2735 Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka, 812-8581, JapanSearch for more papers by this authorHiroyuki Takemura, Hiroyuki Takemura Department of Chemistry, Faculty of Science, Kyushu University, Fukuoka 810-8560, JapanSearch for more papers by this authorKatsuya Sako, Katsuya Sako Department of Systems Management and Engineering, Nagoya Institute of Technology, Nagoya 466-8555, JapanSearch for more papers by this authorHitoshi Tatemitsu, Hitoshi Tatemitsu Department of Systems Management and Engineering, Nagoya Institute of Technology, Nagoya 466-8555, JapanSearch for more papers by this authorTakahiko Inazu, Takahiko Inazu Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka, 812-8581, JapanSearch for more papers by this authorTeruo Shinmyozu, Teruo Shinmyozu shinmyo@ms.ifoc.kyushu-u.ac.jp Institute for Fundamental Research of Organic Chemistry (IFOC), Kyushu University, Fukuoka 812-8581, Japan, Fax: (internat.) + 81-92/642-2735Search for more papers by this author Hajime Isaji, Hajime Isaji Institute for Fundamental Research of Organic Chemistry (IFOC), Kyushu University, Fukuoka 812-8581, Japan, Fax: (internat.) + 81-92/642-2735 Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka, 812-8581, JapanSearch for more papers by this authorMikio Yasutake, Mikio Yasutake Institute for Fundamental Research of Organic Chemistry (IFOC), Kyushu University, Fukuoka 812-8581, Japan, Fax: (internat.) + 81-92/642-2735 Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka, 812-8581, JapanSearch for more papers by this authorHiroyuki Takemura, Hiroyuki Takemura Department of Chemistry, Faculty of Science, Kyushu University, Fukuoka 810-8560, JapanSearch for more papers by this authorKatsuya Sako, Katsuya Sako Department of Systems Management and Engineering, Nagoya Institute of Technology, Nagoya 466-8555, JapanSearch for more papers by this authorHitoshi Tatemitsu, Hitoshi Tatemitsu Department of Systems Management and Engineering, Nagoya Institute of Technology, Nagoya 466-8555, JapanSearch for more papers by this authorTakahiko Inazu, Takahiko Inazu Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka, 812-8581, JapanSearch for more papers by this authorTeruo Shinmyozu, Teruo Shinmyozu shinmyo@ms.ifoc.kyushu-u.ac.jp Institute for Fundamental Research of Organic Chemistry (IFOC), Kyushu University, Fukuoka 812-8581, Japan, Fax: (internat.) + 81-92/642-2735Search for more papers by this author First published: 05 June 2001 https://doi.org/10.1002/1099-0690(200107)2001:13 3.0.CO;2-FCitations: 16Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract Photodecarbonylation of [3.3]cyclophane-2,11-diones, which are readily prepared by TosMIC coupling, affords [2.2]cyclophanes in high yield. This method also provides a general synthetic method for [3.2]cyclophan-2-ones by taking advantage of the fact that this photochemical reaction proceeds in a stepwise manner through [3.2]cyclophan-2-ones. A series of [2.2]cyclophanes, [3.2]cyclophanes, and [3.3]cyclophanes can thus be made available from the common precursor [3.3]cyclophane-2,11-diones. In sharp contrast to the preferred syn geometry of [3.3]metacyclophanes, [3.2]metacyclophanes adopt anti geometries and the aryl ring inversion process is observed by variable-temperature 1H NMR spectroscopy. In the crystalline state, the two aryl rings of anti-[3.2]metacyclophanes are almost parallel in spite of the unsymmetrical bridge length; they overlap only at the C-9 and C-17 positions, and the transannular distances are shorter than the corresponding distances in [3.3]metacyclophane-2,11-dione. Citing Literature Volume2001, Issue13July 2001Pages 2487-2499 RelatedInformation
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