111679-99-3Relevant academic research and scientific papers
PROPARGYL ORGANOMETALLIC COMPOUNDS. II. ALKYLATION OF SODIUM DERIVATIVES OF 1-ALKYL-1-ARYL-2-ALKYNES IN LIQUID AMMONIA
Libman, N. N.,Sevryukov, Yu. P.
, p. 68 - 75 (2007/10/02)
In most cases the alkylation of the sodium derivatives of 1-phenyl-1-alkyl-2-alkynes by methyl, ethyl, isopropyl, and tert-butyl bromides in liquid ammonia takes place preferentially at the sp2-hybridized carbon atom, and this leads to the formation of the corresponding acetylenes.The regioselectivity of the reaction is explained by the greater softness of the trigonal atom of the ambident propargyl anion and its smaller screening by the solvate shell compared with the diagonal atom.
