Issue 24, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Diastereoselective intramolecular [4 + 4] photocycloaddition reaction of N-(naphthylcarbonyl)anthracene-9-carboxamides: temperature effects and reversal of diastereoselectivity

Shigeo Kohmoto,*a   Hyuma Masu,a   Chuya Tatsuno,a   Keiki Kishikawa,a   Makoto Yamamotoa  and  Kentaro Yamaguchib  

* Corresponding authors

a Department of Materials Technology, Faculty of Engineering, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba, Japan

b Chemical Analysis Centre, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba, Japan

Abstract

Intramolecular diastereoselective [4 + 4] photocycloadditions of acyclic imides 1a and 1b possessing anthracene and naphthalene moieties were carried out in the solid state and in solution. For 1a, novel reversal of diastereoselectivity was observed on changing the reaction phase. The diastereomeric excess was changed from −60% de in the solid state at 60 °C to 70% de in acetone at −78 °C. Almost 100% de was observed for the solid-state photocycloaddition of 1b. The reactivity of 1a in the solid state was discussed based on its single crystal X-ray analysis.

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Article information

DOI
https://doi.org/10.1039/B005142J
Article type
Paper
Submitted
27 Jun 2000
Accepted
01 Nov 2000
First published
05 Dec 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 4464-4468

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Diastereoselective intramolecular [4 + 4] photocycloaddition reaction of N-(naphthylcarbonyl)anthracene-9-carboxamides: temperature effects and reversal of diastereoselectivity

S. Kohmoto, H. Masu, C. Tatsuno, K. Kishikawa, M. Yamamoto and K. Yamaguchi, J. Chem. Soc., Perkin Trans. 1, 2000, 4464 DOI: 10.1039/B005142J

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