88106-30-3Relevant academic research and scientific papers
Regioselective Route to Sterically Hindered Cyclopropylcarbinyl Halides
Hrubiec, Robert T.,Smith, Michael B.
, p. 431 - 435 (1984)
Reaction of cyclopropylcarbinyl alcohols 1 with hexachloroacetone and triphenylphosphine resulted in 80 - 90 percent yields of the corresponding cyclopropylcarbinyl chlorides 4 regioselectively, with no trace of the homoallylic chloride 2 or the chlorocyclobutane derivative 6a.Similar reaction of 1 with bromine and triphenylphosphine, in dimethylformamide, gave 65 - 80 percent yields of the cyclopropylcarbinyl bromide 5 with trace amounts of the homoallylic bromide 3 but no detectable bromocyclobutane derivative 6b.These reactions are amenable to the preparation of very sterically hindered cyclopropylcarbonyl halides, heretofore inaccessible, regioselectively and in a facile manner.
Regiospecific Nucleophilic Substitution in Cyclopropylcarbinols. Stereospecific Opening of the Cyclopropane Ring
Matveeva,Kvasha,Kurts
, p. 17 - 20 (2007/10/03)
Reactions of cyclopropylcarbinols with hydrobromic acid and the triphenylphosphine-tetrabromomethane complex at 0°C result in stereospecific opening of the cyclopropane ring with formation of trans-homoallyl bromides.
REACTION DU TRIMETHYL CHLOROSILANE AVEC LES ALCOOLS α-CYCLOPROPANIQUES EN PRESENCE OU EN L'ABSENCE D'HALOGENURES DE LITHIUM.
Balme, Genevieve,Fournet, Guy,Gore, Jacques
, p. 1907 - 1908 (2007/10/02)
α-Cyclopropyl alcohols react with Me3SiCl, eventually in the presence of LiBr or LiI, leading to a cyclopropyl halide or (and) to a homopropargylic halide, according to the nature of the alcohol.
