Abstract
Photochemical reaction of 2,3-dihydrothiophene 1,1-dioxide [2-sulfolene] with maleic anhydride gives the [2 + 2] cycloadduct 8 and simple reactions of the anhydride function provide access to a wide range of new bi- and tri-cyclic sulfones 9-13 and 15-24 containing the novel 2-thiabicyclo[3.2.0]heptane 2,2-dioxide ring system. On pyrolysis these undergo either cycloreversion with elimination of 2-sulfolene or in one case extrusion of ethene and SO2 to give the 1,3-diene. Oxidative bis-decarboxylation of the diacid from hydrolysis of 8 gives the new simple alkene sulfone 31. Pyrolysis of this results in loss of only SO2 to give cyclohexa-1,3-diene, but its epoxide 34 loses SO2 and ethene to afford furan, thus making 31 a synthetic equivalent of cyclobutadiene.
Original language | English |
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Pages (from-to) | 1983-1989 |
Number of pages | 7 |
Journal | Journal of the Chemical Society, Perkin Transactions 1 |
Issue number | 14 |
DOIs | |
Publication status | Published - 21 Jul 1994 |
Keywords
- 3,3-DIOXIDE