849730-01-4Relevant academic research and scientific papers
Nucleophilic and electrophilic substitutions of difluoropropargyl bromides
Hammond, Gerald B.
, p. 476 - 488 (2006)
Fundamental organic reactions like nucleophilic and electrophilic substitutions have seldom been studied on fluorinated propargyl or allenyl modules, when the carbon atom undergoing substitution is bonded to two fluorine atoms. Herein we report a practical synthesis of difluoropropargyl bromides from substituted acetylenes and dibromodifluorometane using a wide variety of alkyl, aryl or silyl substrates. The synthesis of O-, S- and carboxylic acid derivatives of difluoropropargyl bromide is also described. These compounds are suitable starting materials for the synthesis of electrophilically substituted difluoropropargyl derivatives via magnesium and fluoride promoted reactions. An indium-mediated reaction of silyldifluoropropargyl bromide, followed by electrophilic trapping with bromine led to a very useful bromoallene, which was then used in reactions with nucleophiles (C, O, N, P, S, Hal) to yield a de facto bimolecular nucleophilic substitution of a difluoropropargyl bromide.
Characterization of gem-difluoropropargyl synthons through HF loss from protonated molecules in methane chemical ionization mass spectra
Hammond, Gerald B.,Mae, Masayuki,Hong, Jiyoung A.,Hurst, Harrell E.
, p. 126 - 132 (2006)
Electron impact and methane chemical ionization mass spectra were obtained following gas chromatography/mass spectrometry for several gem-difluoropropargyl compounds, which had been synthesized as potential intermediates for synthesis of gem-difluoromethy
Mg(0)-promoted debromometalation of gem-difluoropropargyl bromides
Mae, Masayuki,Hong, Jiyoung A.,Hammond, Gerald B.,Uneyama, Kenji
, p. 1787 - 1789 (2007/10/03)
Mg(0)/Me3SiCl was found to be effective for the preparation of difluoropropargylsilanes. This method, using Me3SnCl, produced the corresponding propargylstannane.
