Complete ozonolysis of alkyl substituted ethenes at -60 °C: distributions of ozonide and oligomeric products.

Matthew Barton, John R. Ebdon, Andrew B. Foster, Steve. Rimmer

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The distribution of ozonide and oligomeric structures formed on complete ozonolysis of alkenes in a non-participating solvent at -60° is governed by the alkyl substitution around the carbon-carbon double bond. The ozonolysis of a 1,1-alkyl substituted ethene generally favors the formation of an ozonide (a 1,2,4-trioxolane). Whereas the ozonolysis of a 1,1,2-alkyl substituted ethene also produces ozonide, a considerable amt. of the ozonized products are oligomeric in nature. For example, the ozonolysis of 3-methylpent-2-ene in soln. to high conversion in pentane yields oligomers with structural units derived from the fragmentation products of the primary ozonide (a 1,2,3-trioxolane) which are namely butanone carbonyl oxide and acetaldehyde; these can be characterized by electrospray ionization mass spectroscopy (ESI-MS) under soft ionization conditions. The predominant oligomers formed are rich in carbonyl oxide units (80 + mol%) and are cyclic in nature. A small proportion of the oligomers formed are open chain compds. with end groups that suggest that chain termination is brought about either by water or by hydrogen peroxide. Residual water in the solvent will react with the carbonyl oxides to produce 2-methoxybut-2-yl hydroperoxide, which we propose readily decomps. generating hydrogen peroxide. A significant yield of oligomers also is obtained from the ozonolysis of a 1,2-alkyl substituted ethene. The ozonolysis of trans-hex-2-ene in pentane yields oligomers contg. up to four structural units and are predicted to be mainly cyclic. [on SciFinder(R)]
    Original languageEnglish
    Pages (from-to)1323-1329
    Number of pages7
    JournalOrganic & biomolecular chemistry
    Volume3
    Issue number7
    DOIs
    Publication statusPublished - 2005

    Keywords

    • ozonolysis alkene ozonide oligomer

    Fingerprint

    Dive into the research topics of 'Complete ozonolysis of alkyl substituted ethenes at -60 °C: distributions of ozonide and oligomeric products.'. Together they form a unique fingerprint.

    Cite this