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Literature DB >> 24700600

Generation of C(2)F(5)CHN(2) in situ and its first reaction: [3+2] cycloaddition with alkenes.

Abstract

The novel chemical reagent, C2 F5 CHN2 , is generated in situ from C2 F5 CH2 NH2 ⋅HCl and sodium nitrite. It reacts with mono- and disubstituted electron-deficient alkenes at room temperature to afford C2 F5 -pyrazolines in excellent yields.

Entities: Chemical

Keywords: cycloaddition; diazo compounds; fluorine; in situ generation; pyrazolines

Mesh：

Substances：

Year: 2014 PMID： 24700600 DOI： 10.1002/chem.201304840

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

4 in total

1. SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride-Amine Adducts.

Authors: Hua Wang; Feng Zhou; Gerui Ren; Qinheng Zheng; Hongli Chen; Bing Gao; Liana Klivansky; Yi Liu; Bin Wu; Qingfeng Xu; Jianmei Lu; K Barry Sharpless; Peng Wu
Journal: Angew Chem Int Ed Engl Date: 2017-05-18 Impact factor: 15.336

2. SuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride.

Authors: Pavel Yamanushkin; Kemal Kaya; Mark Aldren M Feliciano; Brian Gold
Journal: J Org Chem Date: 2022-02-10 Impact factor: 4.198

3. Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes.

Authors: Pavel K Mykhailiuk
Journal: Beilstein J Org Chem Date: 2015-01-06 Impact factor: 2.883

Review 4. Diazoacetonitrile (N₂ CHCN): A Long Forgotten but Valuable Reagent for Organic Synthesis.

Authors: Pavel K Mykhailiuk; Rene M Koenigs
Journal: Chemistry Date: 2019-10-15 Impact factor: 5.236