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Dehydrogenation of Perfluoroalkyl Ketones by Using a Recyclable Oxoammonium Salt
Author(s) -
Hamlin Trevor A.,
Kelly Christopher B.,
Leadbeater Nicholas E.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300392
Subject(s) - dehydrogenation , chemistry , tetrafluoroborate , salt (chemistry) , reaction mechanism , organic chemistry , medicinal chemistry , polymer chemistry , catalysis , ionic liquid
A novel dehydrogenation reaction of perfluoroalkyl ketones by the oxoammonium salt 4‐acetylamino‐2,2,6,6‐tetramethylpiperidine‐1‐oxoammonium tetrafluoroborate (4‐NHAc‐TEMPO + BF 4 – , Bobbitt's salt, 1 ) is described. The reaction proceeds under mildly basic conditions and appears to be unique to perfluoroalkyl ketones. A proposed mechanism for this unusual transformation is given. The byproduct of the reaction, 4‐acetylamino‐2,2,6,6‐tetramethyl‐1‐piperidinyloxy ( 1a ), can easily be recovered and used to regenerate the oxoammonium salt.