Jump to main content
Jump to site search

Issue 8, 1994
Previous Article Next Article

Effect of ring strain on the formation and pyrolysis of some Diels–Alder adducts of 2-sulfolene (2,3-dihydrothiophene 1,1-dioxide) and maleic anhydride with 1,3-dienes and products derived therefrom

Abstract

7-Thiabicyclo[4.3.0]non-3-ene 7,7-dioxide 3 and the 2,5-bridged analogues 46 formed by Diels–Alder reaction of 2,3-dihydrothiophene 1,1-dioxide (2-sulfolene)2 with butadiene and cyclic 1,3-dienes are found, upon flash vacuum pyrolysis, either to lose SO2 and ethene, or to undergo a retro-Diels–Alder reaction, depending on the degree of ring strain present. The epoxides 10, 13 and 17 of these compounds decompose exclusively by loss of SO2 and ethene to give the mono-epoxides of cyclic 1,4-dienes which undergo further reactions under the pyrolysis conditions. The same final products can also be obtained by extrusion of CO and CO2 from the epoxides 12, 16 and 19 of the corresponding diene–maleic anhydride adducts. In the case of the furan–maleic anhydride adduct, its epoxide 20 fragments by a retro-Diels–Alder reaction to give 1,4-dioxine, which, at high temperatures, is transformed into acrylaldehyde. Pyrolysis of the aziridines 2224, formed by photochemical reaction of the diene–maleic anhydride adducts with ethyl azidoformate, generally gives complex decomposition products, although for the methylene-bridged compound 22 there is good evidence for the generation of a 1,4-dihydropyridine via a retro-Diels–Alder reaction.

Back to tab navigation
Please wait while Download options loads

Article type: Paper
DOI: 10.1039/P19940000927
Citation: J. Chem. Soc., Perkin Trans. 1, 1994, 927-931
  •   Request permissions

    Effect of ring strain on the formation and pyrolysis of some Diels–Alder adducts of 2-sulfolene (2,3-dihydrothiophene 1,1-dioxide) and maleic anhydride with 1,3-dienes and products derived therefrom

    R. A. Aitken, J. I. G. Cadogan and I. Gosneya, J. Chem. Soc., Perkin Trans. 1, 1994, 927
    DOI: 10.1039/P19940000927

Search articles by author