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Markovnikov Regiocontrol in Hydroboration of Alkene by Trifluoromethyl Substituent
Author(s) -
Fan YuBo,
Wang QuanRui,
Ding ZongBiao,
Tao FengGang
Publication year - 2001
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20010190317
Subject(s) - chemistry , regioselectivity , alkene , trifluoromethyl , hydroboration , substituent , markovnikov's rule , ene reaction , boranes , computational chemistry , stereochemistry , medicinal chemistry , boron , organic chemistry , alkyl , catalysis
The reaction of dichloroborane BHCl 2 with 3,3,3‐trifluoro‐prop‐1‐ene (TFP), and propene have been studied using B3LYP method with 6–31G + basis set. Based on the calculations, all transition structures have parallelogram‐like H‐B‐C‐C four‐center geometry with small deformations. The introduction of fluorine atoms changes the proportions of hydroborational products and reverses the regioselectivity.