Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes

The Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic 1,3-dienes was investigated. A series of novel monofluorinated norbornenes was prepared in up to 97% yield. The reaction with 1,3-cyclohexadiene permits the preparation of monofluorinated bicyclo[2.2.2]oct-2-enes. The kinetic data of t...

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Main Authors:	Savva A. Ponomarev, Roman V. Larkovich, Alexander S. Aldoshin, Andrey A. Tabolin, Sema L. Ioffe, Jonathan Groß, Till Opatz, Valentine G. Nenajdenko
Format:	Article
Language:	English
Published:	Beilstein-Institut 2021-01-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	diels–alder reaction fluorine nitrostyrene norbornene stereochemistry
Online Access:	https://doi.org/10.3762/bjoc.17.27

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spelling	doaj-44e21075ae3d4f0bb200ba3830fbd4152021-02-08T09:47:07ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-01-0117128329210.3762/bjoc.17.271860-5397-17-27Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienesSavva A. Ponomarev0Roman V. Larkovich1Alexander S. Aldoshin2Andrey A. Tabolin3Sema L. Ioffe4Jonathan Groß5Till Opatz6Valentine G. Nenajdenko7Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1, Moscow, 119991, Russian FederationDepartment of Chemistry, Lomonosov Moscow State University, Leninskie gory 1, Moscow, 119991, Russian FederationDepartment of Chemistry, Lomonosov Moscow State University, Leninskie gory 1, Moscow, 119991, Russian FederationN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences Leninsky prosp. 47, Moscow 119991, Russian FederationN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences Leninsky prosp. 47, Moscow 119991, Russian FederationDepartment of Chemistry Johannes Gutenberg-University, Duesbergweg 10–14, D-55128 Mainz, GermanyDepartment of Chemistry Johannes Gutenberg-University, Duesbergweg 10–14, D-55128 Mainz, GermanyDepartment of Chemistry, Lomonosov Moscow State University, Leninskie gory 1, Moscow, 119991, Russian FederationThe Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic 1,3-dienes was investigated. A series of novel monofluorinated norbornenes was prepared in up to 97% yield. The reaction with 1,3-cyclohexadiene permits the preparation of monofluorinated bicyclo[2.2.2]oct-2-enes. The kinetic data of the reactions with 1,3-cyclopentadiene and 1,3-cyclohexadiene were used to calculate activation parameters. Furthermore, the synthetic utility of the cycloadducts obtained was demonstrated.https://doi.org/10.3762/bjoc.17.27diels–alder reactionfluorinenitrostyrenenorbornenestereochemistry
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Savva A. Ponomarev Roman V. Larkovich Alexander S. Aldoshin Andrey A. Tabolin Sema L. Ioffe Jonathan Groß Till Opatz Valentine G. Nenajdenko
spellingShingle	Savva A. Ponomarev Roman V. Larkovich Alexander S. Aldoshin Andrey A. Tabolin Sema L. Ioffe Jonathan Groß Till Opatz Valentine G. Nenajdenko Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes Beilstein Journal of Organic Chemistry diels–alder reaction fluorine nitrostyrene norbornene stereochemistry
author_facet	Savva A. Ponomarev Roman V. Larkovich Alexander S. Aldoshin Andrey A. Tabolin Sema L. Ioffe Jonathan Groß Till Opatz Valentine G. Nenajdenko
author_sort	Savva A. Ponomarev
title	Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
title_short	Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
title_full	Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
title_fullStr	Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
title_full_unstemmed	Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
title_sort	diels–alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2021-01-01
description	The Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic 1,3-dienes was investigated. A series of novel monofluorinated norbornenes was prepared in up to 97% yield. The reaction with 1,3-cyclohexadiene permits the preparation of monofluorinated bicyclo[2.2.2]oct-2-enes. The kinetic data of the reactions with 1,3-cyclopentadiene and 1,3-cyclohexadiene were used to calculate activation parameters. Furthermore, the synthetic utility of the cycloadducts obtained was demonstrated.
topic	diels–alder reaction fluorine nitrostyrene norbornene stereochemistry
url	https://doi.org/10.3762/bjoc.17.27
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Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes

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