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Synlett 2010(16): 2383-2391  
DOI: 10.1055/s-0030-1258559
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Organosulfur Compounds Based on Cyclocondensation Reactions of 3-Arylthio-1-silyloxy-1,3-butadienes and 1,3-Bis(silyloxy)-1,3-butadienes

Muhammad Nawaza, Muhammad Shera,b,c, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
b Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
c Department of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan
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Publikationsverlauf

Received 5 February 2010
Publikationsdatum:
03. September 2010 (online)

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Abstract

Cyclocondensation reactions of sulfur-containing dienes, such as 3-arylthio-1-silyloxy-1,3-butadienes and 4-arylthio-1,3-bis(trimethylsilyloxy)-1,3-butadienes, with various dielectrophiles and dieneophiles allow for a convenient synthesis of a variety of functionalized and sterically encumbered aryl-substituted sulfides and sulfones which are not readily available by other methods. The building block strategy outlined herein is advantageous for the synthesis of highly substituted, sterically encumbered and functionalized molecules compared to methods which rely on the formation of a carbon-sulfur bond.

1 Introduction

2 3-Arylthio-1-trimethylsilyloxy-1,3-butadienes

2.1 Synthesis of 3-Arylthio-1-trimethylsilyloxy-1,3-butadienes

2.2 [3+3] Cyclocondensations of 3-Arylthio-1-trimethylsilyl­oxy-1,3-butadienes

2.2.1 1,1,3,3-Tetramethoxypropane

2.2.2 3-Silyloxy-2-en-1-ones

2.2.3 3-Alkoxy-2-en-1-ones

2.2.4 3-Ketoacetals

2.2.5 1,1-Diacylcyclopropanes

2.2.6 3-Oxo-orthoesters

2.2.7 1,1-Bis(methylthio)-1-en-3-ones

2.3 [4+2] Cycloadditions of 1-Arylthio-3-trimethylsilyloxy-1,3-butadienes

2.3.1 Dimethyl Acetylenedicarboxylate

2.3.2 Dimethyl Allene-1,3-dicarboxylate

2.4 Michael-Type Reactions of 1-Arythio-3-trimethylsilyloxy-1,3-butadienes

3 Cyclocondensations of 1,3-Bis(silyloxy)-1,3-butadienes with Sulfur-Containing Dielectrophiles

3.1 Reactions of 3-Alkoxy- and 3-Silyloxy-2-en-1-ones

3.1.1 2-Arylthio-3-silyloxy-2-en-1-ones

3.1.2 2-Arylthio-3-alkoxy-2-en-1-ones

3.1.3 2-Arylsulfonyl-3-alkoxy-2-en-1-ones

3.2 Reactions of 1,1-Bis(methylthio)-1-en-3-ones

4 4-Arylthio-1,3-bis(trimethylsilyloxy)-1,3-butadienes

4.1 Synthesis of 4-Arylthio-1,3-bis(trimethylsilyloxy)-1,3-butadienes

4.2 [3+3] Cyclizations of 4-Arylthio-1,3-bis(trimethylsilyl­oxy)-1,3-butadienes

4.2.1 1,1,3,3-Tetramethoxypropane

4.2.2 3-Silyloxy-2-en-1-ones

4.2.3 1,1-Diacetylcyclopropane

4.3 Cyclizations of 4-Arylthio-1,3-bis(silyloxy)-1,3-butadienes with Chromones

4.3.1 Formylchromone

4.3.2 Chromone

5 Conclusions

Key words

arenes - cyclizations - organosulfur compounds - silyl enol ethers

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