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Synlett 1992; 1992(1): 22-24
DOI: 10.1055/s-1992-21251
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Synthesis and Reactions of Some Tosylhydrazones of Tricyclo [5.3.0.02,6] decadiones

Hans-Jürgen Bister* , Holger Butenschön
  • *Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-4330 Mülheim a.d. Ruhr, Germany
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Publication Date:
18 September 2002 (online)

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Tricyclo[5.3.0.02,6]deca-3,8-dienes (5) and -3,9-dienes (8) are obtained by Shapiro reactions from tosylhydrazones 4 (3,8-bis(tosylhydrazono)tricyclo[5.3.0.02,6]decanes) and 7 (3,10-bis(tosylhydrazono)tricyclo[5.3.0.02,6]decanes) in gram quantities. The tricyclo[5.3.0.02,6]deca-4,9-diene-3,8-dione bis(tosylhydrazone) (10) can be prepared in 49% yield from the known dienenone 9. Reaction of 10 with lithium bases does not lead to elimination products but gives dilithium salt 11. Differential scanning calorimetry (DSC) analysis shows a reaction of 11 above 120 °C. Trapping with dimethyl fumarate leads to the new double spiro-annulated pentacycle 13a,b (2′,2″,3′,3″- tetramethoxycarbonyldispiro [tricyclo[5.3.0.02,6]deca-4,9-diene-3,8-dicyclopropane]). Trapping with iron pentacarbonyl generates fulvalene-diiron complex 14 [tetracarbonyl(η5:η5-pentafulvalene)diiron] as the result of an elimination/isomerisation sequence.

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