General Papers ARKIVOC 2006 (x) 173-182
Bromofluorocarbene addition to 6-phenylbicyclo[3.2.0]hept-6-ene: characterization and formation mechanism of the products
Fatih Algia,b and Metin Balcia,*
aDepartment of Chemistry, Middle East Technical University, 06531, Ankara,Turkey bDepartment of Chemistry, Onsekiz Mart University, 17020, Canakkale,Turkey E-mail: mbalci@metu.edu.tr
Abstract
Bromofluorocarbene addition to 6-phenylbicyclo[3.2.0]hept-6-ene provided fluoro-indanes such as 4,6-difluoro-5-phenylindane, 5,6-difluoro-4-phenylindane, 5,7-difluoro-4-phenylindane, 4bromo- 6-fluoro-5-phenylindane and 5-bromo-6-fluoro-4-phenylindane. The characterization the formation mechanism of the products are discussed.
Keywords: Bromofluorocarbene, carbene addition, fluoro-indanes
Introduction
Carbenes are versatile intermediates that undergo insertion, rearrangement and facile addition reactions in which their importance to synthetic chemists can hardly be overestimated.1 The most common and thoroughly investigated reaction of carbenes is their addition to carbon-carbon double bonds, which provide ready access to cyclopropane derivatives and/or the corresponding rearranged products. Our contribution to this field is exemplified with the synthesis of bromofluoro cyclopropanes 1, 2 and 3, which were successfully converted to corresponding strained cyclic allenes and in turn stimulated us to attain further insights into this class of compounds.2-4 It is also worth noting that only a few carbene reactions with small-ring alkenes have been reported.5,6 Albeit numerous studies with open chain and cyclic alkenes larger than four-membered rings do in fact exist. Therefore, we have turned our attention to an unsymmetrical cyclobutene appendage 4 in connection with our work directed toward the synthesis of strained small-ring allenes.7 Herein, we would like to report the results of the bromofluoro carbene addition to 6-phenylbicyclo[3.2.0]hept-6-ene (4).8
ISSN 1424-6376 Page 173 ©ARKAT
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