122171-44-2Relevant academic research and scientific papers
Stereochemistry and mechanism of cyclopropane formation from ionization of C5H5(CO)2Fe(CH2)3X
Casey, Charles P.,Smith Vosejpka, Laura J.
, p. 738 - 744 (2008/10/08)
Cyclopropane was produced efficiently both in the Ag+-assisted dissociation of bromide from C5H5(C-O)2Fe(CH2)3Br (1) and in the dissociation of phenyl methyl sulfide from C5H5(CO)2Fe(CH2) 3S-(CH3)C6H5+CF 3SO3- (8). Clean inversion of stereochemistry at the carbon bound to iron was seen in the formation of cis-1,2-dideuteriocyclopropane from the threo sulfonium salt C5H5(CO)2FeCHDCHDCH2S-(CH 3)C6H5+CF3SO 3- (threo-8-d2). This stereochemical result is consistent with a W-shaped transition state for cyclopropane formation and rules out a mechanism involving a metallacyclobutane intermediate. A new explanation for the selective formation of cis cyclopropanes from the reaction of alkenes with (C-O)5W=CHC6H5 is proposed in light of the results reported here.
Inversion of stereochemistry at the carbon bound to iron in cyclopropane formation from threo-C5H5(CO)2FeCHDCHDCH2S(CH 3)C6H5+
Casey, Charles P.,Smith, Laura J.
, p. 2288 - 2290 (2008/10/08)
Upon heating at 65°C, threo-C5H5-(CO)2FeCHDCHDCH2S(CH 3)C6H5+CF3SO 3- is converted to cis-1,2-dideuteriocyclopropane with inversion of
