Neues über den Mechanismus der retentiven Substitution am Dreiring von Propellanen. Vorläufige Mitteilung |
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Authors: | Hans J rg Lindner,Brigitte Kitschke,Michael Liesner,Dieter Seebach |
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Affiliation: | Hans Jörg Lindner,Brigitte Kitschke,Michael Liesner,Dieter Seebach |
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Abstract: | New results concerning the mechanism of retentive substitution at the three membered ring of propellanes The reaction of the endo- and exo-bromide 1a and 1b with acetate ion in aprotic polar solvents carried out at high concentrations of 1 furnishes the dimeric dehydro-halogenation products 3a and 3b , the structures of which are determined by x-ray crystallography (Fig. 1). The formation of 3a and 3b as well as of the products 2 of a retentive substitution process can be explained by assuming that the strained benzo-tropones 4 are intermediates. Their high barrier to inversion is confirmed by π-SCF-molecular mechanics calculations. |
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