Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 167, Issue -, Pages 152-158Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2014.07.008
Keywords
Fluorinated iminophosphonates; gem-Difluoroimines; Phosphonates; Electrophilic fluorination
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Funding
- Wroclaw Research Centre EIT+ under the project Biotechnologies and advanced medical technologies - BioMed - European Regional Development Fund (Operational Programme Innovative Economy) [POIG.01.01.02-02-003/08, 1.1.2]
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A method for the first synthesis of alpha,alpha-difluoromethylene-beta-iminophosphonates has been developed. The strategy is based on electrophilic fluorination of secondary beta-enaminophosphonates derived from beta-ketophosphonate precursor and the corresponding primary amines. However, in case of fluorination of N-alkyl beta-enaminophosphonate, the dephosphorylation has been observed yielding N-alkyl difluoromethylimine. The obtained product structures and geometry of beta-enamine/imine double bonds were determined by H-1, C-13, F-19 and P-31 NMR spectroscopy. (C) 2014 Elsevier B.V. All rights reserved.
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