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New Metal-Free One-Pot Synthesis of Substituted Allenes from Enones

Meng Tang, Chun-An Fan, Fu-Min Zhang, Yong-Qiang Tu*, Wen-Xue Zhang and Ai-Xia Wang

*State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China, Email: tuyqlzu.edu.cn

M. Tang, C.-A. Fan, F.-M. Zhang, Y.-Q. Tu, W.-X. Zhang, A.-X. Wang, Org. Lett., 2008, 10, 5585-5588.

DOI: 10.1021/ol802445p (free Supporting Information)


Abstract

A metal-free, one-pot synthesis of substituted allenes from enones via the corresponding α,β-unsaturated tosylhydrazones proceeds readily with high compatibility of sensitive functional groups using a tertiary amine as a base. This synthetic protocol provides synthetically important allenes without the use of metallic reagents or catalysts.

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proposed mechanism



Key Words

Allenes


ID: J54-Y2008-3810