Sterically Crowded Hexaalkyl Benzene-1,2,3,4,5,6-hexakis[α-(alkoxycarbonyl)propanoates]. Synthesis and Conformation Analysis

[img]PDF - Authorized users only
Language: English
1263Kb
Title:Sterically Crowded Hexaalkyl Benzene-1,2,3,4,5,6-hexakis[α-(alkoxycarbonyl)propanoates]. Synthesis and Conformation Analysis
Creators:
Alexander, Daniel
Böhm, Stanislav
Císařová, Ivana
Holý, Petr
Podlaha, Jaroslav
Šlouf, Miroslav
Závada, Jiří
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 5, pp. 673-694
Uncontrolled Keywords:Molecular mechanics, Multiarmed compounds, Alkylations, Benzenes, Conformation analysis, X-Ray diffraction, Malonates, Carbanions, Semiempirical calculations

Abstract

A selective hexa-fold monoalkylation of the malonester carbanion <sup>(-)</sup>CH(COOR)<sub>2</sub> (R = Me, Et, <i>t</i>-Bu, Bn) with hexakis(bromomethyl)benzene afforded the title compounds <strong>3</strong> in a high-yield reactions. On subsequent replacement of the acid α-hydrogens with bulkier substituents, the title compounds <strong>3</strong>, R = Et, provided a broad variety of the α-X-persubstituted homologues and derivatives <strong>4</strong> (X = Me, Et, Bu, Oc, Bn, Br, N<sub>3</sub>). The effect of the variable X substituent on conformation was investigated by single-crystal X-ray diffraction and compared with the results obtained by theoretical calculation. <p>

Title:Sterically Crowded Hexaalkyl Benzene-1,2,3,4,5,6-hexakis[α-(alkoxycarbonyl)propanoates]. Synthesis and Conformation Analysis
Creators:
Alexander, Daniel
Böhm, Stanislav
Císařová, Ivana
Holý, Petr
Podlaha, Jaroslav
Šlouf, Miroslav
Závada, Jiří
Uncontrolled Keywords:Molecular mechanics, Multiarmed compounds, Alkylations, Benzenes, Conformation analysis, X-Ray diffraction, Malonates, Carbanions, Semiempirical calculations
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:65
Number:5
Page Range:pp. 673-694
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000673UNSPECIFIED
ID Code:1671
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Alexander, Daniel; Böhm, Stanislav; Císařová, Ivana; Holý, Petr; Podlaha, Jaroslav; Šlouf, Miroslav; Závada, Jiří (2000) Sterically Crowded Hexaalkyl Benzene-1,2,3,4,5,6-hexakis[α-(alkoxycarbonyl)propanoates]. Synthesis and Conformation Analysis. Collection of Czechoslovak Chemical Communications, 65 (5). pp. 673-694. ISSN 0010-0765

Repository Staff Only: item control page