engleski

Reactivity increase of dienophiles by change of the ester substituents into the acid chlorides: Cycloaddition reaction of the Diacid Chloride of 3, 10-hexacyclo[10.2.1.15, 8.02, 11.03, 10.04, 9] hexadeca-6, 13-diene-3, 10-dicarboxylic acid with quadricyclane

Conversion of the ester substituents on the cyclobutene p-bond of dimethyl tricyclo[4.2.1.02, 5]nona-3, 7-diene-3, 4-dicarboxylate to the corresponding acid chloride increases the cycloaddition reactivity toward quadricyclane so dramatically that the reaction temperature can be dropped from 180
C (preparation of title 3, 10-diester) to room temperature (preparation of the title 3, 10-diacid chloride). The cycloadduct product, an acid chloride of the title ring system, is extremely docile and can be recrystallized unchanged from hot methanol.

polynorbornanes; acid chloride; polycycles; guadricyclane; DFT calculations

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