Experimental and theoretical studies on the transannular cyclizations of 3,7-dimethylenebicyclo[3.3.1]nonane with polyfluoroalkyl radicals期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

Experimental and theoretical studies on the transannular cyclizations of 3,7-dimethylenebicyclo[3.3.1]nonane with polyfluoroalkyl radicals

Authors:	Maxim V. Ponomarenko Bogdan V. Ponomarenko Andrey A. Fokin

Affiliation:	^a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanskaya Str., 02094 Kiev, Ukraine ^b Institute of Inorganic & Physical Chemistry, University of Bremen, Leobener Strasse, 28334 Bremen, Germany ^c National Technical University of Ukraine “Kiev Polytechnic Institute”, 37 Pobeda Ave, 03056 Kiev, Ukraine

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:	Cyclization 3,7-Dimethylenebicyclo[3.3.1]nonane Perfluoroalkyl iodide Ethyl iododifluoroacetate Diethyl iododifluorophosphonate Noradamantane derivatives Ab initio calculations
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