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Synthesis 2011(15): 2377-2382  
DOI: 10.1055/s-0030-1260089
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© Georg Thieme Verlag Stuttgart ˙ New York

TBAF-Promoted Elimination of Vicinal Dibromides Having an Adjacent O-Functional Group: Syntheses of 2-Bromoalk-1-enes and Alkynes

Noriki Kutsumura*, Keisuke Kubokawa, Takao Saito*
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
Fax: +81(3)52614631; e-Mail: nkutsu@rs.kagu.tus.ac.jp; e-Mail: tsaito@rs.kagu.tus.ac.jp;
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Publication History

Received 4 April 2011
Publication Date:
28 June 2011 (online)

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Abstract

Syntheses of 2-bromoalk-1-enes and alkynes were achieved in good yields by dehydrobromination of vicinal dibromides with tetrabutylammonium fluoride. Neighboring O-functional-group participation is important in determining elimination reactivity.

Key words

tetrabutylammonium fluoride - elimination - 2-bromo­alk-1-enes - alkynes - vicinal dibromides

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