tele Nucleophilic Substitutions of Hydrogen in m-(Trichloromethyl)nitrobenzenes with Cyano and Ester Carbanions

 
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2010 (EN)
tele Nucleophilic Substitutions of Hydrogen in m-(Trichloromethyl)nitrobenzenes with Cyano and Ester Carbanions (EN)

Surowiec, M. (EN)

Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας (EL)
Surowiec, M. (EN)

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)

carbanions (EN)

Πανεπιστήμιο Ιωαννίνων (EL)
University of Ioannina (EN)

European Journal of Organic Chemistry (EN)

English

2010

<Go to ISI>://000279746300017

Wiley-VCH Verlag (EN)



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