877080-72-3Relevant articles and documents
Highly regioselective synthesis of gem-difluoroallenes through magnesium organocuprate SN2′ substitution
Mae, Masayuki,Hong, Jiyoung A.,Xu, Bo,Hammond, Gerald B.
, p. 479 - 482 (2007/10/03)
The reaction of gem-difluoropropargyl electrophiles with Grignard reagents is complicated by the inherent difficulty of executing nucleophilic substitutions on a CF2 group, and the facile formation of carbenoid intermediates arising from α-elimination of fluoride. In the presence of an excess amount of a copper salt, a Grignard reagent reacts with gem-difluoropropargyl bromide via an SN2′ mechanism to produce gem-difluoroallene in high yield. If desired, the resulting difluoroallene can undergo a second nucleophilic attack on the CF2 terminus to yield a trisubstituted monofluoroallene through an addition-elimination mechanism.
Crystallographic characterization of difluoropropargyl indium bromide, a reactive fluoroorganometallic reagent
Xu, Bo,Mashuta, Mark S.,Hammond, Gerald B.
, p. 7265 - 7267 (2008/04/18)
Elusive intermediate trapped: γ-Substituted difluoropropargyl groups can stabilize an organoindium(III) complex. The resulting structure is the only known example of an indium atom bonded to a propargylic carbon atom (see picture; F blue, S yellow, C white, H green). Reactions with electrophiles produced a difluoroalkyne or -allene, depending on the type of electrophile. (Chemical Equation Presented).
