Issue 3, 2003
From the journal:

Organic & Biomolecular Chemistry

Synthesis, absolute configuration and conformation of optically active 1,2-homoheptafulvalene†

Shunji Ito,a   Mitsuhiro Kurita,a   Sigeru Kikuchi,a   Toyonobu Asao,a   Yoshitora Ito,a   Masaji Oda,b   Hideo Sotokawa,c   Akio Tajirid  and  Noboru Morita*a  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Tohoku University, Aobaku, Sendai 980-8578, Japan

b Department of Chemistry, Graduate School of Science, Osaka University, Machikaneyama 1-1, Toyonaka, Osaka 560-0043, Japan

c Production Engineering Research Laboratory, Hitachi Ltd., Yoshida-cho 292, Totsuka-ku, Yokohama, 244-0817, Japan

d Department of Materials Science, Faculty of Science and Technology, Hirosaki University, Hirosaki 036-8561, Japan

Abstract

An optically active 1,2-homoheptafulvalene was successfully synthesized and subjected to spectroscopic investigation. The cycloaddition of the optically active hydrocarbon with tetracyanoethylene (TCNE) and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) gave a [4 + 2] cycloadduct and a mixture of [8 + 2] cycloadducts, respectively, which are both optically active.

Graphical abstract: Synthesis, absolute configuration and conformation of optically active 1,2-homoheptafulvalene

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Article information

DOI
https://doi.org/10.1039/B210949M
Article type
Paper
Submitted
06 Nov 2002
Accepted
12 Dec 2002
First published
15 Jan 2003

Org. Biomol. Chem., 2003,1, 488-492

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Synthesis, absolute configuration and conformation of optically active 1,2-homoheptafulvalene

S. Ito, M. Kurita, S. Kikuchi, T. Asao, Y. Ito, M. Oda, H. Sotokawa, A. Tajiri and N. Morita, Org. Biomol. Chem., 2003, 1, 488 DOI: 10.1039/B210949M

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