Synthesis of hydrohalocyclobutenes through dechlorination of hydrohalocyclobutanes in amide solvents

Wenni Zhang; Fengniu Lu; Chengping Zhang; Qin Guo; Hengdao Quan

doi:10.1016/j.jfluchem.2020.109506

Synthesis of hydrohalocyclobutenes through dechlorination of hydrohalocyclobutanes in amide solvents

Wenni Zhang, Fengniu Lu, Chengping Zhang, Qin Guo, Hengdao Quan^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

In this study, we synthesized hydrohalocyclobutenes through the dechlorination of hydrohalocyclobutanes in N,N-dimethylformamide and N,N-dimethylacetamide. The structure of the reaction site −CClR¹−CClR²– (R¹ = H, F; R² = H, F, Cl) of the reactants was critical for the efficient reductive dechlorination from the 1- and 2- positions. The reaction proceeded efficiently at the –CFCl–CFCl–, –CFCl−CCl₂–, and −CHCl−CHCl– groups. Conversely, the –CFCl−CHCl– group could hardly afford the dechlorinated product. Based on these results, we propose a rational reaction mechanism.

Original language	English
Article number	109506
Journal	Journal of Fluorine Chemistry
Volume	233
DOIs	https://doi.org/10.1016/j.jfluchem.2020.109506
Publication status	Published - May 2020
Externally published	Yes

Keywords

1,2-Dichloro
Dechlorination
Elimination
Hydrohalocyclobutenes
N,N-dimethylacetamide
N,N-dimethylformamide

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10.1016/j.jfluchem.2020.109506

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Zhang, W., Lu, F., Zhang, C., Guo, Q., & Quan, H. (2020). Synthesis of hydrohalocyclobutenes through dechlorination of hydrohalocyclobutanes in amide solvents. Journal of Fluorine Chemistry, 233, Article 109506. https://doi.org/10.1016/j.jfluchem.2020.109506

@article{85653285af7e4508b1d35f7df8a1e786,

title = "Synthesis of hydrohalocyclobutenes through dechlorination of hydrohalocyclobutanes in amide solvents",

abstract = "In this study, we synthesized hydrohalocyclobutenes through the dechlorination of hydrohalocyclobutanes in N,N-dimethylformamide and N,N-dimethylacetamide. The structure of the reaction site −CClR1−CClR2– (R1 = H, F; R2 = H, F, Cl) of the reactants was critical for the efficient reductive dechlorination from the 1- and 2- positions. The reaction proceeded efficiently at the –CFCl–CFCl–, –CFCl−CCl2–, and −CHCl−CHCl– groups. Conversely, the –CFCl−CHCl– group could hardly afford the dechlorinated product. Based on these results, we propose a rational reaction mechanism.",

keywords = "1,2-Dichloro, Dechlorination, Elimination, Hydrohalocyclobutenes, N,N-dimethylacetamide, N,N-dimethylformamide",

author = "Wenni Zhang and Fengniu Lu and Chengping Zhang and Qin Guo and Hengdao Quan",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier B.V.",

year = "2020",

month = may,

doi = "10.1016/j.jfluchem.2020.109506",

language = "English",

volume = "233",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

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TY - JOUR

T1 - Synthesis of hydrohalocyclobutenes through dechlorination of hydrohalocyclobutanes in amide solvents

AU - Zhang, Wenni

AU - Lu, Fengniu

AU - Zhang, Chengping

AU - Guo, Qin

AU - Quan, Hengdao

PY - 2020/5

Y1 - 2020/5

N2 - In this study, we synthesized hydrohalocyclobutenes through the dechlorination of hydrohalocyclobutanes in N,N-dimethylformamide and N,N-dimethylacetamide. The structure of the reaction site −CClR1−CClR2– (R1 = H, F; R2 = H, F, Cl) of the reactants was critical for the efficient reductive dechlorination from the 1- and 2- positions. The reaction proceeded efficiently at the –CFCl–CFCl–, –CFCl−CCl2–, and −CHCl−CHCl– groups. Conversely, the –CFCl−CHCl– group could hardly afford the dechlorinated product. Based on these results, we propose a rational reaction mechanism.

AB - In this study, we synthesized hydrohalocyclobutenes through the dechlorination of hydrohalocyclobutanes in N,N-dimethylformamide and N,N-dimethylacetamide. The structure of the reaction site −CClR1−CClR2– (R1 = H, F; R2 = H, F, Cl) of the reactants was critical for the efficient reductive dechlorination from the 1- and 2- positions. The reaction proceeded efficiently at the –CFCl–CFCl–, –CFCl−CCl2–, and −CHCl−CHCl– groups. Conversely, the –CFCl−CHCl– group could hardly afford the dechlorinated product. Based on these results, we propose a rational reaction mechanism.

KW - 1,2-Dichloro

KW - Dechlorination

KW - Elimination

KW - Hydrohalocyclobutenes

KW - N,N-dimethylacetamide

KW - N,N-dimethylformamide

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U2 - 10.1016/j.jfluchem.2020.109506

DO - 10.1016/j.jfluchem.2020.109506

M3 - Article

AN - SCOPUS:85082129273

SN - 0022-1139

VL - 233

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

M1 - 109506

ER -

Synthesis of hydrohalocyclobutenes through dechlorination of hydrohalocyclobutanes in amide solvents

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Keywords

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