Ozonides halogens

Halo-2-vinylacetylenes. Chlorine, bromine iodine vinylacetylenes can be prpd by the reaction, at 0°, of the halogen in aq KOH with monovinylacetylene (Ref 1). All polymerize.in air to form explosive polymers, with the I-compds being the most explosive of the three. Polymerization is also accelerated by UV, ozonides,... 

Rule 6 among stereoisomeric ozonides, the trans isomers (or the compounds which should be trans from the lower retention time) are always fragmentated faster than the cis isomers (Table XIII). The trans/cis factor, however, usually is not large. Only with halogen containing substituents does it exceed 10. 

Ozonolysis of the monobromide 8 in ethyl acetate occurred also preferably at the non-halogenated double bond to form the ozonide 9(5) ... 

The oxidation of alkenes and cycloalkenes and their halogen derivatives with at least one hydrogen or halogen atom at the double bond leads to carboxylic acids. Ozonolysis usually requires the oxidative decomposition of the ozonide. The oxygen content of the ozonide is not sufficient for the formation of two molecules of acids or one dicarboxylic acid. The nonoxidative decomposition of cyclohexene ozonide gives an aldehyde-acid or its derivatives [1108]. It comes, therefore, as a surprise that carboxylic acids are claimed as products of the decomposition of ozonides by hydrogenation over the Lindlar catalyst [55] (equation 108). 

In contrast, epoxides, ozonides, and certain halogen derivatives are characterized by anionized name forms of the added atoms (or groups of atoms) placed behind the stem terms. It should be noted, though, that retention of this method is not recommended when other types of nomenclature (substitutive or heterocycle nomenclature) permit unambiguous simpler names. 

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