Simple methods for the preparation of N-triflyl guanidines and the structure of compounds with the CF3SO2NCN fragment

Two novel and simple approaches to N-triflyl guanidines are elaborated. The formally double CN bond in TfNC(NHHex-c)2 is longer than the formally single NC bonds. [Display omitted] ► N-triflyl guanidines from triflamide and urea and from ► N-sulfinyltriflimide and carbodiimides. ► Strong conjugation...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2012-03, Vol.135, p.261-264
Main Authors: Shainyan, Bagrat A., Tolstikova, Ljudmila L., Schilde, Uwe
Format: Article
Language:English
Subjects:
MP2 calculations
N-triflyl guanidines
Structure
Synthesis
X-ray
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Summary:Two novel and simple approaches to N-triflyl guanidines are elaborated. The formally double CN bond in TfNC(NHHex-c)2 is longer than the formally single NC bonds. [Display omitted] ► N-triflyl guanidines from triflamide and urea and from ► N-sulfinyltriflimide and carbodiimides. ► Strong conjugation in N-triflyl guanidines makes the formally double CN bond longer than the formally single bonds. Two novel and simple approaches to N-triflyl guanidines are elaborated. Owing to very strong conjugation the formally double CN bond of TfNC(NHR)2 is longer than the formally single NC bonds. Energetic effect of the triflyl group on the conjugation in the NCN moiety is estimated to be ≥150kcal/mol.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2011.12.004