Artigo Revisado por pares

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

ISSN

1434-193X

Autores

H. Isaji, M. Yasutake, Hiroyuki Takemura, Katsuya Sako, Hitoshi Tatemitsu, Takahiko Inazu, Teruo Shinmyozu,

Tópico(s)

Supramolecular Chemistry and Complexes

Resumo

European 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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