Title of article
Experimental and theoretical studies on the transannular cyclizations of 3,7-dimethylenebicyclo[3.3.1]nonane with polyfluoroalkyl radicals
Author/Authors
Ponomarenko، نويسنده , , Maxim V. and Serguchev، نويسنده , , Yurii A. and Ponomarenko، نويسنده , , Bogdan V. and Rِschenthaler، نويسنده , , Gerd-Volker and Fokin، نويسنده , , Andrey A.، نويسنده ,
Issue Information
روزنامه با شماره پیاپی سال 2006
Pages
8
From page
842
To page
849
Abstract
Radical cyclizations of 3,7-dimethylenebicyclo[3.3.1]nonane with CF3I, n-C3F7I, ICF2COOEt and ICF2PO(OEt)2 selectively led to corresponding 3,7-noradamantanes, which were used for preparation of various polyfluoroalkyl substituted noradamantyl amines and carboxylates. DFT computations revealed that chemoselectivity of the radical cyclizations is realized due to the high electrophilicity of the CF3 radical, as well as due to efficient trapping of intermediate noradamantylmethyl radicals by perfluoroiodoalkane.
Keywords
Diethyl iododifluorophosphonate , Ethyl iododifluoroacetate , Noradamantane derivatives , Ab initio calculations , cyclization , 3 , Perfluoroalkyl iodide
Journal title
Journal of Fluorine Chemistry
Serial Year
2006
Journal title
Journal of Fluorine Chemistry
Record number
1609286
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