tele Nucleophilic Substitutions of Hydrogen in m-(Trichloromethyl)nitrobenzenes with Cyano and Ester Carbanions
| dc.contributor.author | Surowiec, M. | en |
| dc.contributor.author | Belekos, D. | en |
| dc.contributor.author | Makosza, M. | en |
| dc.contributor.author | Varvounis, G. | en |
| dc.date.accessioned | 2015-11-24T16:50:01Z | |
| dc.date.available | 2015-11-24T16:50:01Z | |
| dc.identifier.issn | 1434-193X | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/9559 | |
| dc.rights | Default Licence | - |
| dc.subject | carbanions | en |
| dc.subject | michael addition | en |
| dc.subject | arenes | en |
| dc.subject | nucleophilic substitution | en |
| dc.subject | elimination | en |
| dc.subject | c-nucleophiles | en |
| dc.subject | nitroarenes | en |
| dc.subject | transformations | en |
| dc.subject | chemistry | en |
| dc.subject | salts | en |
| dc.subject | ring | en |
| dc.title | tele Nucleophilic Substitutions of Hydrogen in m-(Trichloromethyl)nitrobenzenes with Cyano and Ester Carbanions | en |
| heal.abstract | Stabilized carbanions of malonates, 2-phenylacetonitrile, or isopropyl 2-phenylacetate add to m-(trichloromethyl)nitrobenzene derivatives to form sigma(H) adducts that lose a chloride ion to give intermediate exo-dichloromethylene nitrocyclohexadienes. These undergo re-aromatization through 1,5-hydrogen shift to yield tele substitution mono adducts. Depending on the stoichiometry of the nitroarene to the carbanion, further addition of the nucleophile to the tele mono adduct can yield a mixture of products that are either double or triple adducts. At low temperature, the ail adducts undergo direct 1,2-addition in competition with chloride ion elimination/1,5-hydrogen shift. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | DOI 10.1002/ejoc.200901303 | - |
| heal.identifier.secondary | <Go to ISI>://000279746300017 | - |
| heal.identifier.secondary | http://onlinelibrary.wiley.com/store/10.1002/ejoc.200901303/asset/3501_ftp.pdf?v=1&t=hmrgi8bh&s=3518642090e13c0b13990accbb2929e048fc9091 | - |
| heal.journalName | European Journal of Organic Chemistry | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 2010 | - |
| heal.publisher | Wiley-VCH Verlag | en |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |
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