Orienting Effect of the Cage Addends: The Case of Nucleophilic Cyclopropanation of C2 -C70 (CF3 )8

Chemistry, an Asian Journal
Marina G ApenovaAlexey A Goryunkov

Abstract

C2 -C70 (CF3 )8 was found to be a very promising substrate in the Bingel and the Bingel-Hirsch reactions combining perfect regioselectivity with much higher reactivity compared to its analogs. The reactions with diethyl malonate yield a single isomer of the monoadduct C70 (CF3 )8 [C(CO2 Et)2 ] and a single C2 -symmetrical bisadduct C70 (CF3 )8 [C(CO2 Et)2 ]2 . The Bingel-Hirsch variation is particularly interesting in that it additionally affords, in a similar regioselective manner, the unexpected alkylated derivatives C70 (CF3 )8 [CH(CO2 Et)2 ]H and C70 (CF3 )8 [C(CO2 Et)2 ][CH(CO2 Et)2 ]H. The novel compounds have been isolated and structurally characterized by means of (1) H and (19) F NMR spectroscopy as well as single-crystal X-ray diffraction. The mechanistic and regiochemical aspects of the reaction are explained with the aid of DFT calculations.

References

Oct 28, 1996·Physical Review Letters·J P PerdewM Ernzerhof
May 16, 2000·The Journal of Organic Chemistry·H P SpielmannM S Meier
Feb 19, 2002·Chemical Reviews·Alan L. Balch, Marilyn M. Olmstead
Aug 17, 2002·The Journal of Organic Chemistry·Mark S MeierZhongwen Wang
Jun 5, 2003·Angewandte Chemie·Sergey I TroyanovErhard Kemnitz
Mar 22, 2006·Chemistry : a European Journal·Eugenii I DorozhkinOlga V Boltalina
Apr 13, 2006·Chemical Communications : Chem Comm·Daria V Ignat'evaSergey I Troyanov
Mar 7, 2007·Organic & Biomolecular Chemistry·Valentina P GubskayaIldus A Nuretdinov
Mar 26, 1993·Science·C C Henderson, P A Cahill
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Aug 12, 2009·The Journal of Organic Chemistry·Yuta TakanoNazario Martín
Mar 9, 2010·Chemistry : a European Journal·Yuta TakanoTakeshi Akasaka
Dec 15, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Natalia S OvchinnikovaErhard Kemnitz
Oct 24, 2013·The Journal of Physical Chemistry. a·Daria V Ignat'evaLev N Sidorov
Nov 20, 2013·Chemistry : a European Journal·Nataliya A SamoylovaAlexey A Goryunkov

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Citations

May 10, 2016·Chemistry, an Asian Journal·Victor A BrotsmanAlexey A Goryunkov

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