An Acid Catalysed Intramolecular C–C Coupling Reaction of 8-halomethyl-16-methoxy[2.2]Metacyclophanes-Reference-Cited by-同舟云学术

An Acid Catalysed Intramolecular C–C Coupling Reaction of 8-halomethyl-16-methoxy[2.2]Metacyclophanes

Published:2005-08 Issue:8 Volume:2005 Page:495-497
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Tanaka Kan¹,Miyazawa Akira¹,Hiate Ai²,Tashiro Masashi²³,Saisyo Tatsunori⁴,Okabe Ryo⁴,Kohno Kazufumi⁴,Yamato Takehiko⁴

Affiliation:

1. National Institute of Advanced Industrial Science and Technology (AIST), AIST Central 5, Tsukuba, Ibaraki 305-8565, Japan

2. Institute of Advanced Material Study, Kyushu University, Kasuga-kouen 6-1, Kasuga 816-8580, Japan

3. Present address: Loker Hydrocarbon Research Institute, University of Southern California, 837 Bloom Walk LHI, Los Angeles Calfornia 90089-1661, USA

4. Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga 840-8502, Japan

Abstract

The hydrolysis of 8-bromomethyl[2.2]metacyclophane 1a with a methoxy group at the 16-position was carried out in an 80% aqueous dioxane solution by refluxing in the presence of Nafion-H (a solid perfluorinated resin sulfonic acid) as a catalyst. The reaction yielded the corresponding 8-hydroxymethyl[2.2]metacyclophane 3 and the intramolecular C–C coupling product 2 with a spiro skeleton.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/030823405774663228

Reference19 articles.

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2. Some Chemistry of [2.2]Metacyclophane. A Transannular Electrophilic Aromatic Substitution Reaction1

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4. Iodine-induced transformation of [2,2]metacyclophanes to 1,2,3,3a,4,5,-hexahydropyrenes: a highly selective cycloisomerization reaction involving intermolecular hydrogen transfer

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