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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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Bibliographic Details
Published in:European journal of organic chemistry 2017-07, Vol.2017 (27), p.3935-3940
Main Authors: Khutorianskyi, Andrii, Chalyk, Bohdan, Borysko, Petro, Kondratiuk, Anna, Mykhailiuk, Pavel K.
Format: Article
Language:English
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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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700764