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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 9: 2760 - 2776

DOI: https://doi.org/10.6023/cjoc202405015

ARTICLES

Study of BF3•Et2O-Promoted Rearrangement of Cyclopropenylcarbinols

  • Miaomiao Xun ,
  • Jingjing Guo ,
  • Wenbing Ma ,
  • Yuqiang Li ,
  • Changchun Yuan ,
  • Kai Fu
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  • a School of Chemistry and Chemical Engineering, North University of China, Taiyuan, Shanxi 030051
    b Dezhou Industrial Technology Research Institute of North University of China, Dezhou, Shandong 253000
*E-mail: ;

Received date: 2024-05-13

  Revised date: 2024-07-17

  Online published: 2024-08-19

Supported by

Natural Science Foundation of Shandong Province(ZR2023MB043); National Natural Science Foundation of China(22371266)

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Abstract

γ-Ylidenebutenolides and benzofulvenes are of considerable importance in natural product and medicinal chemistry. Cyclopropenylcarbinols were promoted by BF3•Et2O to induce the C—C bond cleavage reaction of cyclopropenes via dehydroxylation to form an allene carbocation intermediate. This leads to the construction of γ-ylidenebutenolide and benzofulvene compounds in one pot via different isomerization rearrangement paths. This synthetic strategy expands the synthesis methods of two types of compounds, achieving a total yield of 68%~99%. In addition, the electronic effect and reaction temperature considerably influence the ratio of the two compounds. Moreover, the reaction provides a new method for precise C—C bond cleavage of cyclopropenes.

Key words： cyclopropene; BF3•Et2O; γ-alkylidenebutenolide; benzofulvene; C—C bond cleavage

Cite this article

Miaomiao Xun , Jingjing Guo , Wenbing Ma , Yuqiang Li , Changchun Yuan , Kai Fu . Study of BF3•Et2O-Promoted Rearrangement of Cyclopropenylcarbinols[J]. Chinese Journal of Organic Chemistry, 2024 , 44(9) : 2760 -2776 . DOI: 10.6023/cjoc202405015

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