Reintroducing Azidodifluoromethane: Synthesis, Stability and [3+2] Cycloadditions. Issue 37 (30th July 2018)

• Record Type: Journal Article
• Authors: Voltrová, Svatava; Putovný, Igor; Matoušek, Václav; Klepetářová, Blanka; Beier, Petr
• Other Names: Hostomský Zdeněk guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 37(2018)
• Page Start: 5087
• Page End: 5090
• Publication Date: 2018-07-30
• Subjects: Fluorinated compounds -- Azides -- Fluorine -- Difluoromethyl group -- Triazoles -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800650
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Azidodifluoromethane was prepared in 65 % yield from chlorodifluoromethane by a two‐step synthesis using tributyl(difluoromethyl)ammonium chloride as an intermediate. The resulting azide was used in Huisgen azide‐alkyne reactions and ketone [3+2] cycloadditions to access novel N ‐difluoromethyl‐1, 2, 3‐triazoles. Abstract : Novel N ‐difluoromethyl‐1, 2, 3‐triazoles were synthesized through Huisgen's azide–alkyne reaction and a ketone [3+2] cycloaddition by using azidodifluoromethane – a versatile N ‐difluoromethyl building block obtained by a two‐step synthesis from chlorodifluoromethane via the quaternary trialkyldifluoromethylammonium salt.