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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 21
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Original Articles

New Application of N-Halosuccinimide/PPh3 for the Halogenation of Propargyl Alcohols to Haloallenes

Xin Du State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, China
,
Yao Dai State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, China
,
Ren He State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, China
,
Shirong Lu State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, China
&
Ming Bao State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, ChinaCorrespondence[email protected]
Pages 3940-3949 | Received 05 Oct 2008, Published online: 07 Oct 2009
 
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Abstract

An efficient and convenient new method has been developed for the preparation of haloallenes from propargyl alcohols by a reagent combination of N-halosuccinimide and triphenylphosphine. Chloroallenes 2 and bromoallenes 3 were obtained exclusively in moderate to good yields with regioselectivity.

ACKNOWLEDGMENTS

We are grateful to the National Natural Science Foundation of China (20572010) for financial support. This work was partly supported by the Program for Changjiang Scholars and Innovative Research Teams in Universities (IRT0711).

Notes

a All products are unknown compounds and were characterized by IR, 1H and 13C NMR, and HRMS.

b Isolated yields.

a All products are unknown compounds and were characterized by IR, 1H and 13C NMR, and HRMS.

b Isolated yields.

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