OZONOLYSIS OF VINYL FLUORIDE - IDENTIFICATION OF OZONIDES AND DOUBLY FLUORINATED PRODUCTS

A number of products have been identified upon ozonolysis of vinyl fluoride at low temperatures either neat or in CH3Cl. The major volatile products are formyl fluoride and vinyl fluoride ozonide (3-fluoro-l, 2, 4-trioxolane). Small amounts of both cross ozonides have been observed and trace amounts of acetyl fluoride, fluoroacetyl fluoride, and cj's-l, 2-difluorooxirane. The formation of the three ozonides is consistent with a Criegee pathway involving both H2COO and HFCOO intermediates. The other products can be accounted for by further reactions of intermediates derived from a Criegee pathway or by other unrelated processes. The decomposition of vinyl fluoride ozonide leads to additional volatile products including CO2, HCOF, HCOOH, SiF4 (in glass), and two minor compounds identified as bis(fluoromethyl) ether and fluoromethyl formate. The characterization of vinyl fluoride ozonide and fluoromethyl formate (CH2F0C(0)H) by IR, NMR, mass, and microwave spectroscopy is reported. © 1979, American Chemical Society. All rights reserved.