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It is a terminal alkyne, in fact the smallest that is liquid at room temperature. The compound is a common terminal alkyne substrate in diverse studies of catalysis.
It is a terminal alkyne. A colorless liquid, 1-decyne is used as a model substrate when evaluating methodology in organic synthesis . It participates in a number of classical reactions including Suzuki-Miyaura couplings , Sonogashira couplings , [ 1 ] Huisgen cycloadditions , [ 2 ] and borylations .
Terminal alkynes have the formula RC≡CH, where at least one end of the alkyne is a hydrogen atom. An example is methylacetylene (propyne using IUPAC nomenclature). They are often prepared by alkylation of monosodium acetylide. [4] Terminal alkynes, like acetylene itself, are mildly acidic, with pK a values of around 25.
In organic chemistry, alkynylation is an addition reaction in which a terminal alkyne (−C≡CH) is added to a carbonyl group (C=O) to form an α-alkynyl alcohol (R 2 C(−OH)−C≡C−R). [1] [2] When the acetylide is formed from acetylene (HC≡CH), the reaction gives an α-ethynyl alcohol. This process is often referred to as ethynylation.
The name comes from mix of propene and argentum, which refers to the typical reaction of the terminal alkynes with silver salts. The term homopropargylic designates in the same manner a saturated position on a molecular framework next to a propargylic group and thus two bonds from an alkyne moiety. [1]
Hydroaluminations of terminal alkynes typically produce terminal alkenylalanes as a result. Selectivity in hydroaluminations of internal alkynes is typically low, unless an electronic bias exists in the substrate (such as a phenyl ring in conjugation with the alkyne).
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The coupling of a terminal alkyne and an aromatic ring is the pivotal reaction when talking about applications of the copper-promoted or copper-free Sonogashira reaction. The list of cases where the typical Sonogashira reaction using aryl halides has been employed is large, and choosing illustrative examples is difficult.