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Difluoromethyl Nitrile Oxide (CF2HCNO): A Neglected Chemical Reagent
A novel chemical reagent – difluoromethyl nitrile oxide, CF2HCNO – was generated in situ for the first time. The synthesis commenced with ethyl difluoroacetate and included only two chemical steps. The difluoromethyl nitrile oxide smoothly participated in [3+2]‐cycloaddition reactions with alkynes a...
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Published in: | European journal of organic chemistry 2017-07, Vol.2017 (27), p.3935-3940 |
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Main Authors: | , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | A novel chemical reagent – difluoromethyl nitrile oxide, CF2HCNO – was generated in situ for the first time. The synthesis commenced with ethyl difluoroacetate and included only two chemical steps. The difluoromethyl nitrile oxide smoothly participated in [3+2]‐cycloaddition reactions with alkynes and enamines to give CF2H‐isoxazoles; these products are promising cores for agrochemistry. A representative CHF2‐isoxazole was incorporated into the known fungicide Fluxapyroxad (BASF), and the synthesized analogue showed higher antifungal activity than the parent fungicide.
A novel chemical reagent – difluoromethyl nitrile oxide, CF2HCNO – is finally prepared! Its first reaction, cycloaddition with enamines and alkynes, gives CF2H‐isoxazoles, which are promising cores for agrochemistry. |
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ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201700764 |