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Synthesis of macrocycles having tröger base skeletons “[2.2]cyclic tröger base”

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Abstract

[2.2]Cyclic Tröger base2 was synthesized by the condensation of 1,2-bis (4-aminopheyl) ethane with paraformaldehyde under acidic condition in 43.8% yield. [2.2]Cyclic Tröger base2 was separated into meso form and racemate by fractional crystallization or using HPLC. Resolution of the racemate into its optical antipodes by passing the racemate through an activated D-(+)-lactose column was partially succeeded.

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References and Notes

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Kyushu University 33, Hakozaki, Higashi-ku, 812, Fukuoka

    Masafumi Fukae & Takahiko Inazu

Authors
  1. Masafumi Fukae
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  2. Takahiko Inazu
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Additional information

The trivial name “[2.2]cyclic Tröger base” is used because of the cumbersome nomenclature.

10,12,25,32-Tetraazanonacyclo[19.7.7.14,8.114,18.125,32.07,12.07,12.010,15.-024,34.027,31] octatriaconta-1(29),4,6,8(36),14,16,18(37),21,23,27,-30,34-dodecaene.

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Fukae, M., Inazu, T. Synthesis of macrocycles having tröger base skeletons “[2.2]cyclic tröger base”. Journal of Inclusion Phenomena 2, 223–229 (1984). https://doi.org/10.1007/BF00663260

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