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Catalytic Friedel–Crafts Reactions of Highly Electronically Deactivated Benzylic Alcohols
Author(s) -
Vuković Vuk D.,
Richmond Edward,
Wolf Eléna,
Moran Joseph
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612573
Subject(s) - friedel–crafts reaction , catalysis , chemistry , solvent , brønsted–lowry acid–base theory , alcohol , titration , organic chemistry
Highly electronically deactivated benzylic alcohols, including those with a CF 3 group adjacent to the OH‐bearing carbon, undergo dehydrative Friedel–Crafts reactions upon exposure to catalytic Brønsted acid in 1,1,1,3,3,3‐hexafluoro‐2‐propanol (HFIP) solvent. Titration and kinetic experiments support the involvement of higher order solvent/acid clusters in catalysis.