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3-氟-5-硝基-1-(五氟硫烷基)苯的合成及亲核芳香取代反应

Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene.

作者信息

Ajenjo Javier, Greenhall Martin, Zarantonello Camillo, Beier Petr

机构信息

Institute of Organic Chemistry and Biochemistry, v.v.i., Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.

F2 Chemicals Ltd, Lea Lane, Lea Town, Preston, PR4 0RZ, UK.

出版信息

Beilstein J Org Chem. 2016 Feb 3;12:192-7. doi: 10.3762/bjoc.12.21. eCollection 2016.

DOI:10.3762/bjoc.12.21
PMID:26977178
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4778532/
Abstract

3-Fluoro-5-nitro-1-(pentafluorosulfanyl)benzene was prepared by three different ways: as a byproduct of direct fluorination of 1,2-bis(3-nitrophenyl)disulfane, by direct fluorination of 4-nitro-1-(pentafluorosulfanyl)benzene, and by fluorodenitration of 3,5-dinitro-1-(pentafluorosulfanyl)benzene. The title compound was subjected to a nucleophilic aromatic substitution of the fluorine atom with oxygen, sulfur and nitrogen nucleophiles affording novel (pentafluorosulfanyl)benzenes with 3,5-disubstitution pattern. Vicarious nucleophilic substitution of the title compound with carbon, oxygen, and nitrogen nucleophiles provided 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzenes substituted in position four.

摘要

3-氟-5-硝基-1-(五氟硫烷基)苯可通过三种不同方法制备：作为1,2-双(3-硝基苯基)二硫醚直接氟化的副产物、4-硝基-1-(五氟硫烷基)苯的直接氟化以及3,5-二硝基-1-(五氟硫烷基)苯的氟代脱硝基反应。将标题化合物用氧、硫和氮亲核试剂进行氟原子的亲核芳香取代反应，得到具有3,5-二取代模式的新型(五氟硫烷基)苯。用碳、氧和氮亲核试剂对标题化合物进行替代亲核取代反应，得到在4位被取代的3-氟-5-硝基-1-(五氟硫烷基)苯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/e8a2cc7b8646/Beilstein_J_Org_Chem-12-192-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/297ea659b1bc/Beilstein_J_Org_Chem-12-192-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/a74c666bd7f9/Beilstein_J_Org_Chem-12-192-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/ed6bf07104c0/Beilstein_J_Org_Chem-12-192-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/5286b27a3767/Beilstein_J_Org_Chem-12-192-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/e8a2cc7b8646/Beilstein_J_Org_Chem-12-192-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/297ea659b1bc/Beilstein_J_Org_Chem-12-192-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/a74c666bd7f9/Beilstein_J_Org_Chem-12-192-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/ed6bf07104c0/Beilstein_J_Org_Chem-12-192-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/5286b27a3767/Beilstein_J_Org_Chem-12-192-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6af6/4778532/e8a2cc7b8646/Beilstein_J_Org_Chem-12-192-g006.jpg

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