Simple view

Full metadata view

Authors

Statistics

Titanium(IV) enolates of 2-nitrocarboxylic esters and their oxidative chlorination : a convenient route to α-chloro-α-nitrocarboxylates

2012
journal article
article
10.1055/s-0031-1290081
Journal
Synlett
Author
Cież Dariusz

Kalinowska-Tłuścik Justyna
Volume
23
Number
2
Pages
267-271
ISSN
0936-5214
eISSN
1437-2096
Keywords in English

oxidative chlorination

diastereo­selectivity

titanium enolates

esters

transition states

Language
English
Journal language
English
Abstract in English

A new method for the synthesis of 2-chloro-2-nitrocarboxylic esters from 2-nitrocarboxylates is described. The procedure consists of the oxidative chlorination of titanium(IV) enolates of 2-nitro esters in the presence of ammonium nitrate. Esters of 2-chloro-2-nitrocarboxylic acids are formed in very good to quantitative yields. Application of this method for the chlorination of ,′-dinitrodicarboxylates leads to ,′-dichloro-,′-dinitrocarboxylic esters with high meso-diastereoselectivity. The absence of ammonium nitrate from the reaction mixture affects the reduction of nitro groups and leads to partial transformation of 2-nitrocarboxylic esters into 2-(hydroxyimino)carboxylates.

Affiliation
Wydział Chemii : Zakład Krystalochemii i KrystalofizykiWydział Chemii : Zakład Chemii Organicznej
Scopus© citations
4
dc.abstract.enA new method for the synthesis of 2-chloro-2-nitrocarboxylic esters from 2-nitrocarboxylates is described. The procedure consists of the oxidative chlorination of titanium(IV) enolates of 2-nitro esters in the presence of ammonium nitrate. Esters of 2-chloro-2-nitrocarboxylic acids are formed in very good to quantitative yields. Application of this method for the chlorination of $\alpha$,$\alpha$′-dinitrodicarboxylates leads to $\alpha$,$\alpha$′-dichloro-$\alpha$,$\alpha$′-dinitrocarboxylic esters with high meso-diastereoselectivity. The absence of ammonium nitrate from the reaction mixture affects the reduction of nitro groups and leads to partial transformation of 2-nitrocarboxylic esters into 2-(hydroxyimino)carboxylates.pl
dc.affiliationWydział Chemii : Zakład Krystalochemii i Krystalofizykipl
dc.affiliationWydział Chemii : Zakład Chemii Organicznejpl
dc.contributor.authorCież, Dariusz - 127591 pl
dc.contributor.authorKalinowska-Tłuścik, Justyna - 128600 pl
dc.date.accessioned2015-09-10T10:33:17Z
dc.date.available2015-09-10T10:33:17Z
dc.date.issued2012pl
dc.description.number2pl
dc.description.physical267-271pl
dc.description.points30pl
dc.description.volume23pl
dc.identifier.doi10.1055/s-0031-1290081pl
dc.identifier.eissn1437-2096pl
dc.identifier.issn0936-5214pl
dc.identifier.urihttp://ruj.uj.edu.pl/xmlui/handle/item/15521
dc.languageengpl
dc.language.containerengpl
dc.rightsDodaję tylko opis bibliograficzny*
dc.rights.licenceBez licencji otwartego dostępu
dc.rights.uri*
dc.subject.enoxidative chlorinationpl
dc.subject.endiastereo­selectivitypl
dc.subject.entitanium enolatespl
dc.subject.enesterspl
dc.subject.entransition statespl
dc.subtypeArticlepl
dc.titleTitanium(IV) enolates of 2-nitrocarboxylic esters and their oxidative chlorination : a convenient route to α-chloro-α-nitrocarboxylatespl
dc.title.journalSynlettpl
dc.typeJournalArticlepl
dspace.entity.typePublication
dc.abstract.enpl
A new method for the synthesis of 2-chloro-2-nitrocarboxylic esters from 2-nitrocarboxylates is described. The procedure consists of the oxidative chlorination of titanium(IV) enolates of 2-nitro esters in the presence of ammonium nitrate. Esters of 2-chloro-2-nitrocarboxylic acids are formed in very good to quantitative yields. Application of this method for the chlorination of $\alpha$,$\alpha$′-dinitrodicarboxylates leads to $\alpha$,$\alpha$′-dichloro-$\alpha$,$\alpha$′-dinitrocarboxylic esters with high meso-diastereoselectivity. The absence of ammonium nitrate from the reaction mixture affects the reduction of nitro groups and leads to partial transformation of 2-nitrocarboxylic esters into 2-(hydroxyimino)carboxylates.
dc.affiliationpl
Wydział Chemii : Zakład Krystalochemii i Krystalofizyki
dc.affiliationpl
Wydział Chemii : Zakład Chemii Organicznej
dc.contributor.authorpl
Cież, Dariusz - 127591
dc.contributor.authorpl
Kalinowska-Tłuścik, Justyna - 128600
dc.date.accessioned
2015-09-10T10:33:17Z
dc.date.available
2015-09-10T10:33:17Z
dc.date.issuedpl
2012
dc.description.numberpl
2
dc.description.physicalpl
267-271
dc.description.pointspl
30
dc.description.volumepl
23
dc.identifier.doipl
10.1055/s-0031-1290081
dc.identifier.eissnpl
1437-2096
dc.identifier.issnpl
0936-5214
dc.identifier.uri
http://ruj.uj.edu.pl/xmlui/handle/item/15521
dc.languagepl
eng
dc.language.containerpl
eng
dc.rights*
Dodaję tylko opis bibliograficzny
dc.rights.licence
Bez licencji otwartego dostępu
dc.rights.uri*
dc.subject.enpl
oxidative chlorination
dc.subject.enpl
diastereo­selectivity
dc.subject.enpl
titanium enolates
dc.subject.enpl
esters
dc.subject.enpl
transition states
dc.subtypepl
Article
dc.titlepl
Titanium(IV) enolates of 2-nitrocarboxylic esters and their oxidative chlorination : a convenient route to α-chloro-α-nitrocarboxylates
dc.title.journalpl
Synlett
dc.typepl
JournalArticle
dspace.entity.type
Publication
Affiliations
No affiliation
Cież, Dariusz
Kalinowska-Tłuścik, Justyna

* The migration of download and view statistics prior to the date of April 8, 2024 is in progress.

Views
1
Views per month

No access

No Thumbnail Available
Collections
Research publications