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Synthesis of furan from allenic sulfide derivatives

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Abstract

In this paper, we report the synthesis of furan derivatives from allenic sulfides. By the reaction with NaH, β-Hydroxyl allenic sulfides were found to generate furan products in excellent yields with the removal of phenylthio group. β-Aldehyde allenic sulfides were found to give similar furan products with one more substituent when treated with additional nucleophilic reagents. β-ketone allenic sulfides can also cyclize to give furan derivatives with the promotion of P2O5.

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Authors and Affiliations

  1. College of Chemistry, Peking University, Beijing, China

    LingLing Peng, Xiu Zhang, Jie Ma, ZhenZhen Zhong, Zhe Zhang, Yan Zhang & JianBo Wang

  2. Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory of Molecular Sciences, Beijing, 100871, China

    LingLing Peng, Xiu Zhang, Jie Ma, ZhenZhen Zhong, Zhe Zhang, Yan Zhang & JianBo Wang

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  1. LingLing Peng
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  2. Xiu Zhang
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  3. Jie Ma
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  4. ZhenZhen Zhong
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  5. Zhe Zhang
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  6. Yan Zhang
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  7. JianBo Wang
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Correspondence to JianBo Wang.

Additional information

Supported by the National Natural Science Foundation of China (Grant Nos. 20832002, 20772003 & 20821062), and 973 Project (Grant No. 2009CB825300)

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Peng, L., Zhang, X., Ma, J. et al. Synthesis of furan from allenic sulfide derivatives. Sci. China Ser. B-Chem. 52, 1622–1630 (2009). https://doi.org/10.1007/s11426-009-0224-7

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  • DOI: https://doi.org/10.1007/s11426-009-0224-7

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