Abstract
The reaction of benzo[1′,2′-b]-1,4-diazabicyclo[2.2.2]octene with chloroformate ester is accompanied by opening of the diazabicyclo fragment and addition of chloroformate ester. A nitro group in the 4′ position lowers the rate constant for opening by 40 times in comparison to the unsubstituted heterocycle, while a 4′ methoxy group practically does not affect the reaction rate. The ratio of the 6- and 7- substituted 1-(β-chloroethyl)-4-ethoxycarbonyl-1,2,3,4-tetrahydroquinoxalines which are formed agrees with a quantum chemical calculation of the proton affinity and indicates a principally inductive effect of the substituents on the reactivity of the heteroatoms.
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For Communication 16, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 366–371, March, 1989.
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Gall', A.A., Doronina, S.O., Shishkin, G.V. et al. Diazabicycloalkanes with nitrogen atoms in bridgehead positions.. Chem Heterocycl Compd 25, 305–310 (1989). https://doi.org/10.1007/BF00472391
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DOI: https://doi.org/10.1007/BF00472391