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Reactions of Substituted 2,3,7-Triazabicyclo[3.3.0]oct-2-enes and 1,2,7-Triazaspiro[4.4]non-1-enes with Halogens

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Abstract

Halogenation of 1-substituted 7-aryl-2,3,7-triazabicyclo[3.3.0]oct-2-ene-6,8-diones gives different products, depending on the substituent in position 1 (R1): when R1 = Ar, 6-chloro-3-azabicyclo[3.1.0]hexanes are formed, while compounds with R1 = H or Me give rise to 2- or 4-chloro-2,3,7-triazabicyclo[3.3.0]oct-2-ene-6,8-diones whose thermolysis leads to formation of the corresponding 6-chloro-3-azabicyclo[3.1.0]hexanes. Chlorination of 7-aryl-1,2,7-triazaspiro[4.4]non-1-ene-6,8-diones yields 3-chloro-1,2,7-triazaspiro[4.4]non-1-ene-6,8-diones, and thermolysis of the latter affords 1-chloro-5-azaspiro[2.4]heptanes.

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  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    A. P. Molchanov, A. V. Stepakov & R. R. Kostikov

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  1. A. P. Molchanov
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  2. A. V. Stepakov
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  3. R. R. Kostikov
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 78–88.

Original Russian Text Copyright © 2005 by Molchanov, Stepakov, Kostikov.

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Molchanov, A.P., Stepakov, A.V. & Kostikov, R.R. Reactions of Substituted 2,3,7-Triazabicyclo[3.3.0]oct-2-enes and 1,2,7-Triazaspiro[4.4]non-1-enes with Halogens. Russ J Org Chem 41, 75–86 (2005). https://doi.org/10.1007/s11178-005-0124-z

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  • DOI: https://doi.org/10.1007/s11178-005-0124-z

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