Regio- and Stereoselectivity in Preparation of Benzene Bridged Bis- and Tris-Tröger's Bases

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Title:Regio- and Stereoselectivity in Preparation of Benzene Bridged Bis- and Tris-Tröger's Bases
Creators:
Valík, Martin
Dolensky, Bohumil
Petříčková, Hana
Král, Vladimír
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 5, pp. 609-621
Uncontrolled Keywords:Amines, Tweezers, Supramolecular chemistry, Receptors, Tröger's bases

Abstract

Synthetic strategy for novel multiple Tröger's base derivatives is presented. Compounds were prepared in three steps: <i>o</i>-nitrobenzoylation of benzene-1,2- and -1,3-diamines <strong>3</strong> followed by reduction of nitro and amide groups to amino functions and treatment of the obtained tetraamine compounds <strong>6</strong> with formaldehyde lead to simultaneous formation of bis-Tröger's base (bisTB) derivatives <strong>7a</strong>, <strong>7b</strong>. Only products of 1,2,3,4-substituted regioisomers with <i>anti</i> conformation were separated from reaction mixtures. The same synthetic procedure was used for preparation of tris-Tröger's base (trisTB) derivative <strong>12b</strong> starting from benzene-1,3,5-triamine (<strong>8</strong>). <p>

Title:Regio- and Stereoselectivity in Preparation of Benzene Bridged Bis- and Tris-Tröger's Bases
Creators:
Valík, Martin
Dolensky, Bohumil
Petříčková, Hana
Král, Vladimír
Uncontrolled Keywords:Amines, Tweezers, Supramolecular chemistry, Receptors, Tröger's bases
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:67
Number:5
Page Range:pp. 609-621
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20020609UNSPECIFIED
ID Code:1946
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Valík, Martin; Dolensky, Bohumil; Petříčková, Hana; Král, Vladimír (2002) Regio- and Stereoselectivity in Preparation of Benzene Bridged Bis- and Tris-Tröger's Bases. Collection of Czechoslovak Chemical Communications, 67 (5). pp. 609-621. ISSN 0010-0765

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