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Disiamylborane
 
 
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Disiamylborane (bis(1,2-dimethylpropyl)borane) is an organoborane
Organoborane

Organoborane or organoboron compounds are chemical compounds that are organic derivatives of BH3, for example trialkyl boranes....
 used in organic synthesis
Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
 to add water to a terminal alkyne
Alkyne

Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene is also used to refer specifically to the simplest member of the series, known as e...
, forming an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
 via anti-Markovnikov
Markovnikov's rule

In organic chemistry, Markovnikov's rule or Markownikoff's rule is an observation based on Zaitsev's rule. It was formulated by the Russian chemist Vladimir Vasilevich Markovnikov in 1870 ....
 addition. Disiamylborane is relatively unreactive and will not react with triple-bonded carbons that are not at the terminal position.








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Disiamylborane (bis(1,2-dimethylpropyl)borane) is an organoborane
Organoborane

Organoborane or organoboron compounds are chemical compounds that are organic derivatives of BH3, for example trialkyl boranes....
 used in organic synthesis
Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
 to add water to a terminal alkyne
Alkyne

Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene is also used to refer specifically to the simplest member of the series, known as e...
, forming an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
 via anti-Markovnikov
Markovnikov's rule

In organic chemistry, Markovnikov's rule or Markownikoff's rule is an observation based on Zaitsev's rule. It was formulated by the Russian chemist Vladimir Vasilevich Markovnikov in 1870 ....
 addition. Disiamylborane is relatively unreactive and will not react with triple-bonded carbons that are not at the terminal position.

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