TY - JOUR A1 - Naka, Motoki A1 - Kawasaki-Takasuka, Tomoko A1 - Yamazaki, Takashi T1 - Regioselective carbon–carbon bond formation of 5,5,5-trifluoro-1-phenylpent-3-en-1-yne JF - Beilstein Journal of Organic Chemistry PY - 2013/// VL - 9 SP - 2182 EP - 2188 SN - 1860-5397 DO - 10.3762/bjoc.9.256 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.9.256 KW - additives KW - computation KW - Li···F chelation KW - deprotonation KW - electron-withdrawing effect KW - organo-fluorine N2 - The regioselective carbon–carbon bond formation was studied using 5,5,5-trifluoro-1-phenylpent-3-en-1-yne as a model substrate, and predominant acceptance of electrophiles β to a CF3 group as well as a deuterium trap experiment of the lithiated species led to the conclusion that the obtained regioselectivity is kinetically determined for the reactions with electrophiles, under equilibration of the possible two anionic species. ER -