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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.
For terminal alkynes it is sometimes important to mask the acidic hydrogen atom. This normally proceeds from deprotonation (via a strong base like methylmagnesium bromide or butyllithium in tetrahydrofuran/ dimethylsulfoxide ) and subsequently reaction with chlorotrimethylsilane to a terminally TMS-protected alkyne. [ 95 ]
It is a terminal alkyne. The compound is a common terminal alkyne substrate in diverse studies of catalysis. It is a colorless combustible gas. [1] 1-Butyne participates in reactions typical for terminal alkynes, such as alkyne metathesis, [2] hydrogenation, condensation with formaldehyde.
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.
Usually two equivalents of sodium amide yields the desired alkyne. Three equivalents are necessary in the preparation of a terminal alkynes because the terminal CH of the resulting alkyne protonates an equivalent amount of base. Hydrogen chloride and ethanol can also be eliminated in this way, [11] as in the preparation of 1-ethoxy-1-butyne. [12]
Additionally, LiOH fails to form the necessary adduct with alkynes to initiate the reaction. Hydroxide bases are inexpensive relative to generating an alkoxide or acetylide with reagents such as elemental lithium, sodium, or potassium. Additionally, the stringent reaction conditions used by most alternatives, such as excluding moisture and ...
A hydroboration reaction also takes place on alkynes. Again the mode of action is syn and secondary reaction products are aldehydes from terminal alkynes and ketones from internal alkynes. In order to prevent hydroboration across both the pi-bonds, a bulky borane like disiamyl (di-sec-iso-amyl) borane is used. [5]
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]