Reactions of 2,4,4,6-Tetraaryl-4H-thiopyrans with Chlorine: An Unusual Reaction Route

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Title:Reactions of 2,4,4,6-Tetraaryl-4H-thiopyrans with Chlorine: An Unusual Reaction Route
Creators:
Šebek, Pavel
Kroulík, Jiří
Sedmera, Petr
Havlíček, Vladimír
Kuthan, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 10, pp. 2269-2281

Abstract

<p>2,4,4,6-Tetraaryl-4<i>H</i>-thiopyrans <i>Ia</i> - <i>Ig</i> react smoothly with carbon disulfide solution of chlorine already at 0&nbsp;°C yielding the corresponding 3,5-dichloro derivatives <i>IIa</i> - <i>IIg</i>. With longer reaction time and temperature raised to 20&nbsp;°C, the 4<i>H</i>-thiopyrans <i>Ia</i> - <i>Ie</i> gave exclusively the trichloro derivatives <i>IIIa</i> - <i>IIIe</i> whereas <i>If</i> and <i>Ig</i> underwent a nonselective chlorination leading to multicomponent mixtures of products. Isolation of sulfoxides <i>IVa</i> and <i>IVe</i> from the chlorination of <i>Ia</i> and <i>Ie</i> (upon hydrolysis of the reaction mixture) allowed us to formulate the reaction mechanism for the formation of compounds type <i>III</i>. <sup>1</sup>H, <sup>13</sup>C NMR, and mass spectra of the prepared compounds are discussed in detail.

Title:Reactions of 2,4,4,6-Tetraaryl-4H-thiopyrans with Chlorine: An Unusual Reaction Route
Creators:
Šebek, Pavel
Kroulík, Jiří
Sedmera, Petr
Havlíček, Vladimír
Kuthan, Josef
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:59
Number:10
Page Range:pp. 2269-2281
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19942269UNSPECIFIED
ID Code:649
Item Type:Article
Deposited On:06 Feb 2009 17:02
Last Modified:06 Feb 2009 16:02

Citation

Šebek, Pavel; Kroulík, Jiří; Sedmera, Petr; Havlíček, Vladimír; Kuthan, Josef (1994) Reactions of 2,4,4,6-Tetraaryl-4H-thiopyrans with Chlorine: An Unusual Reaction Route. Collection of Czechoslovak Chemical Communications, 59 (10). pp. 2269-2281. ISSN 0010-0765

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