R. Neidlein, H. Zeiner
Jul 28, 1982
Citations
0
Influential Citations
13
Citations
Journal
Helvetica Chimica Acta
Abstract
Syntheses and Chemical Properties of New ‘Donor-Acceptor’-stahilized Molecular Systems with a Central Bicyclo[4.4.1] undeca-l(10).3,6,8-tetraene-2,5-diylidenc Group The synthesis of X-methyl-2-(5-oxobicyclo[4.4.1]undeca-l)10(,3,6,8-tetraen-2-yliden)-l,3-benzodithiol (4) is described starting with the keto-enol mixture 2 and 5-methyl-1,3-benzodithiolium perchlorate. Under rearomatization of the central frame protonation of 4 yields the salt 4c. The reaction of 4 with dicyanoketene gives the ‘push-pull-substituted’ 5, and with 9-carbonylfluorene the fulvalene derivative 7, which can be protonated by CF3CO2H at C(9″) to the salt 8. The reaction of 2-methylthio-l,3-dithiolium jodide 9 with the keto-enol mixture 2 yields 10, which, on protonation at the carbonyl group by CF3CO2H, gives the salt 11 under rearomatization. The spectral data of the new compounds 4, 4c, 5, 7, 8, 10 and 11 are reported and discussed.