Isopropyl N-Arylmalonamates. Synthesis, Structure, Conformation and Reactions with Carbon Disulfide

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Title:Isopropyl N-Arylmalonamates. Synthesis, Structure, Conformation and Reactions with Carbon Disulfide
Creators:
Rudorf, Wolf-Dieter
Loos, Dušan
Wybraniec, Joanna
Prónayová, Naďa
Gawinecki, Ryszard
Šusteková, Zora
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 1, pp. 59-76
Uncontrolled Keywords:<i>N</i>-Arylmalonamates, Correlation analysis, Ketene dithioacetals, Malonates, AM1 calculations, Conformational analysis

Abstract

Acylation of aromatic amines <strong>1</strong> with diisopropyl malonate (<strong>2</strong>) leads to a mixture of isopropyl <i>N</i>-arylmalonamates <strong>3</strong> and malonanilides <strong>4</strong>. The reaction of <strong>3</strong> with carbon disulfide in the presence of sodium hydride gives disodium salts <strong>5</strong>. Treatment of <strong>5</strong> with an alkylating agent yields the open-chain or cyclic ketene dithioacetals <strong>6</strong>, <strong>7</strong> or <strong>8</strong>. The molecular structure, hydrogen bonding and preferential conformation of the isopropyl <i>N</i>-arylmalonamates <strong>3</strong>, <strong>6</strong> and <strong>7</strong> were investigated using correlation analyses of IR, <sup>13</sup>C NMR and AM1 semiempirical data. <p>

Title:Isopropyl N-Arylmalonamates. Synthesis, Structure, Conformation and Reactions with Carbon Disulfide
Creators:
Rudorf, Wolf-Dieter
Loos, Dušan
Wybraniec, Joanna
Prónayová, Naďa
Gawinecki, Ryszard
Šusteková, Zora
Uncontrolled Keywords:<i>N</i>-Arylmalonamates, Correlation analysis, Ketene dithioacetals, Malonates, AM1 calculations, Conformational analysis
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:71
Number:1
Page Range:pp. 59-76
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20060059UNSPECIFIED
ID Code:2464
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:19

Citation

Rudorf, Wolf-Dieter; Loos, Dušan; Wybraniec, Joanna; Prónayová, Naďa; Gawinecki, Ryszard; Šusteková, Zora (2006) Isopropyl N-Arylmalonamates. Synthesis, Structure, Conformation and Reactions with Carbon Disulfide. Collection of Czechoslovak Chemical Communications, 71 (1). pp. 59-76. ISSN 0010-0765

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