Reaction of tricarbonylcyclo-octatetraene-ruthenium and -iron with electrophilic dienophiles
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in J. Chem. Soc. A
- p. 1172-1175
- https://doi.org/10.1039/j19690001172
Abstract
The electrophilic dienophiles (CF3)2C:C(CN)2, trans-CF3(CN)C:C(CN)(CF3), and (CF3)2C:O react with tricarbonylcyclo-octatetraene-ruthenium and -iron to form 1 : 1 adducts, which on the basis of 1H and 19F n.m.r. measurements, are formulated as arising by a (2 + 2)π reaction, i.e. a 1,2-addition reaction. In contrast, the highly reactive dienophile 4-phenyl-1,2,4-triazole-3,5-(2H,4H)-dione adds 1,4 to tricarbonylcyclo-octatetraene-iron, and the reaction of (CF3)2C:O with C8H8Fe(CO)3 affords an organic ketone C8H8CO[(CF3)2CO]. The analogous ketone C8H8CO[(CF3)2CC(CN)2] is formed by the reaction of C8H8[(CF3)2CC(CN)2]Fe(CO)3 with carbon monoxide, 1,2-diphenylphosphinoethane, and nitric oxide. Possible structures for these compounds are described. The mechanism of the 1,2-addition reactions is discussed.Keywords
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