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Activation of the CF Bond: Transformation of CF 3 NN‐ into 5‐Azidotetrazoles
Author(s) -
Abe Takashi,
Tao GuoHong,
Joo YoungHyuk,
Huang Yangen,
Twamley Brendan,
Shreeve Jean'ne M.
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200802459
Subject(s) - yield (engineering) , bond , conjugated system , transformation (genetics) , chemistry , tetrazole , medicinal chemistry , combinatorial chemistry , stereochemistry , physics , organic chemistry , thermodynamics , business , biochemistry , finance , gene , polymer
N&Ns : The CF bond of trifluoromethylazoalkanes, in the presence of a hydrogen at the α carbon, is activated under basic conditions to form a difluoromethylene intermediate with a conjugated double bond, which is transformed in good yield to the corresponding 5‐azido‐(1‐dialkylimino)tetrazole by reaction with NaN 3 .