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2014•Unpublished venueRequires access

Protection for the Alkyne CH

Peter G. M. Wuts

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Abstract

Protection of acetylenic hydrogen is often necessary because of its acidity. The bulk of a silane can protect acetylene against catalytic hydrogenation because of rate differences between an olefin (primary or secondary) and the more hindered protected alkyne. Trialkylsilylacetylenes are often used as a convenient method for introduction of an acetylenic unit because they tend to be easily handled liquids or solids as opposed to gaseous acetylene. This chapter presents reaction steps for preparing trialkylsilylacetylenes, trimethylsilylalkyne (TMS-alkyne), t-Butyldimethylsilylalkyne (TBDMS), Thexyldimethylsilylalkyne (TDS-alkyne), Benzyldimethylsilylalkyne (BDMS-alkyne), Biphenyldimethylsilylalkyne (BDMS-alkyne), Biphenyldiisopropylsilylalkyne (BDIPS-alkyne) and Tris(biphenyl-4-yl)silyl (TBPS-alkyne).

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What this paper is about

Protection of acetylenic hydrogen is often necessary because of its acidity. The bulk of a silane can protect acetylene against catalytic hydrogenation because of rate differences between an olefin (primary or secondary) and the more hindered protected alkyne. Trialkylsilylacetylenes are often used as a convenient method for introduction of an acetylenic unit because they tend to be easily handled liquids or solids as opposed to gaseous acetylene. This chapter presents reaction steps for preparing trialkylsilylacetylenes, trimethylsilylalkyne (TMS-alkyne), t-Butyldimethylsilylalkyne (TBDMS), Thexyldimethylsilylalkyne (TDS-alkyne), Benzyldimethylsilylalkyne (BDMS-alkyne), Biphenyldimethylsilylalkyne (BDMS-alkyne), Biphenyldiisopropylsilylalkyne (BDIPS-alkyne) and Tris(biphenyl-4-yl)silyl (TBPS-alkyne).

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Available abstract

Protection of acetylenic hydrogen is often necessary because of its acidity. The bulk of a silane can protect acetylene against catalytic hydrogenation because of rate differences between an olefin (primary or secondary) and the more hindered protected alkyne. Trialkylsilylacetylenes are often used as a convenient method for introduction of an acetylenic unit because they tend to be easily handled liquids or solids as opposed to gaseous acetylene. This chapter presents reaction steps for preparing trialkylsilylacetylenes, trimethylsilylalkyne (TMS-alkyne), t-Butyldimethylsilylalkyne (TBDMS), Thexyldimethylsilylalkyne (TDS-alkyne), Benzyldimethylsilylalkyne (BDMS-alkyne), Biphenyldimethylsilylalkyne (BDMS-alkyne), Biphenyldiisopropylsilylalkyne (BDIPS-alkyne) and Tris(biphenyl-4-yl)silyl (TBPS-alkyne).

Key concepts: Alkyne, Acetylene, Silane, Chemistry, Catalysis, Olefin fiber, Medicinal chemistry, Organic chemistry

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