Issue 19, 2000
From the journal:

Chemical Communications

The nucleophilic 5-endo-trigcyclization of gem-difluoroolefins with homoallylic functional groups: syntheses of ring-fluorinated dihydroheteroaromatics

Junji Ichikawa,*a   Masaki Fujiwara,a   Yukinori Wada,a   Tatsuo Okauchib  and  Toru Minami*b  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, Japan.
E-mail: junji@chem.s.u-tokyo.ac.jp;
Fax: Fax: +81-3-5841-4345;
Tel: Phone: +81-3-5841-4345

b Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu, Japan

Abstract

gem-Difluoroolefins bearing homoallylic tosylamido, hydroxy, or mercapto groups undergo intramolecular nucleophilic substitution of the nitrogen, oxygen, or sulfur with loss of fluorine via a 5-endo-trig process, leading to 2-fluoro-2-pyrrolines, 5-fluoro-2,3-dihydrofurans, or -thiophenes in high yields.

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Article information

DOI
https://doi.org/10.1039/B004978F
Article type
Communication
Submitted
21 Jun 2000
Accepted
15 Aug 2000
First published
18 Sep 2000

Chem. Commun., 2000, 1887-1888

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The nucleophilic 5-endo-trig cyclization of gem-difluoroolefins with homoallylic functional groups: syntheses of ring-fluorinated dihydroheteroaromatics

J. Ichikawa, M. Fujiwara, Y. Wada, T. Okauchi and T. Minami, Chem. Commun., 2000, 1887 DOI: 10.1039/B004978F

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