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Synthesis 2002(16): 2319-2334
DOI: 10.1055/s-2002-35231
DOI: 10.1055/s-2002-35231
REVIEW
© Georg Thieme Verlag Stuttgart · New York
The 2-(Trimethylsilyl)ethyl Sulfur Group in Synthesis
Weitere Informationen
Received
11 September 2002
Publikationsdatum:
04. November 2002 (online)
Publikationsverlauf
Publikationsdatum:
04. November 2002 (online)
Abstract
The trimethylsilylethyl sulfur group present in 2-(trimethylsilyl)ethyl sulfides, sulfones, sulfoxides and in 2-(trimethylsilyl)ethylsulfonamido derivatives has proved its potential in synthesis. Presence of sulfur and silicon on adjacent carbon atoms provides routes for preparing interesting sulfur or non-sulfur, silicon or non-silicon derivatives like thiols, methyl disulfides, thioesters, thiocyanates, unsaturated derivatives and amines through the selective removal of the trimethylsilylethyl or the trimethylsilyl group.
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1 Introduction
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2 Synthesis and Reactions of 2-(Trimethylsilyl)ethyl Sulfides
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2.1 Synthesis of 2-(Trimethylsilyl)ethanethiol and Derivatives
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2.2 Reactions of 2-(Trimethylsilyl)ethyl Sulfides
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2.2.1 Synthesis of Non-silylated Thiols and Disulfides
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2.2.2 Other Reactions of 2-(Trimethylsilyl)ethyl Sulfides
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2.2.2.1 Synthesis of 2-(Trimethylsilyl)ethyl Sulfinimides
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2.2.2.2 Removal of the 2-(Trimethylsilyl)ethyl Group and Synthesis of Sulfur Derivatives
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3 2-(Trimethylsilyl)ethyl Sulfones and Sulfoxides
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3.1 Sulfones
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3.2 Sulfoxides
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4 2-(Trimethylsilyl)ethylsulfonamido Derivatives
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4.1 The 2-(Trimethylsilyl)ethylsulfonamido Protecting Group
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4.2 2-(Trimethylsilyl)ethylsulfonamide (SES-NH2)
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4.3 The SES-NH-Boc Derivative
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4.4 N-Sulfinyl-[2-(trimethylsilyl)ethyl]sulfonamide
(SES-NSO) -
4.5 Di[2-(trimethylsilyl)ethyl]sulfodiimide
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4.6 Other Reagents for the Synthesis of SES-protected Amines
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5 Conclusion
Key words
2-(trimethylsilyl)ethyl - sulfur - sufones - sulfoxides - vinyl anion - alkenes - dienes - alkynes - 2-(trimethylsilyl)ethylsulfonamido
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