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2 Li + C 4 H 9 X → C 4 H 9 Li + LiX where X = Cl, Br. The lithium for this reaction contains 1-3% sodium. When bromobutane is the precursor, the product is a homogeneous solution, consisting of a mixed cluster containing both LiBr and LiBu. 1-Fluorobutane can be obtained by reacting 1-bromobutane with potassium fluoride in ethylene glycol. [5]
The intermediate 1-bromo-3-chlorocyclobutane can also be prepared via a modified Hunsdiecker reaction from 3-chlorocyclobutanecarboxylic acid using mercuric oxide and bromine: [4] A synthetic approach to bicyclobutane derivatives involves ring closure of a suitably substituted 2-bromo-1-(chloromethyl)cyclopropane with magnesium in THF. [5]
Theoretical DFT calculations of the reaction between hexafluoro-2-butyne and dienes 3a-c were performed. The reaction starting with [4+2] cycloaddition of CF 3 C≡CCF 3 at one of the furan moieties occurs in a concerted fashion via TS1 and represents the rate limiting step of the whole process with the activation barrier ΔG ‡ ≈ 23.1–26. ...
H 2 C=CH 2 + HBr → H 3 C-CH 2 Br. Bromoethane is inexpensive and would rarely be prepared in the laboratory. A laboratory synthesis includes reacting ethanol with a mixture of hydrobromic and sulfuric acids. An alternate route involves refluxing ethanol with phosphorus and bromine; phosphorus tribromide is generated in situ. [4]
The second part of the reaction converts the isolable gem-dibromoalkene intermediate to the alkyne. Deuterium-labelling studies show that this step proceeds through a carbene mechanism. Lithium-Bromide exchange is followed by α-elimination to afford the carbene. 1,2-shift then affords the deuterium-labelled terminal alkyne. [3]
Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, [1] which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane .
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2-Butyne is of interest to physical chemists because of its very low torsional barrier and the problem of determining that barrier using high-resolution infrared spectroscopy. Analysis of its spectrum [3] leads to a determination that the torsional barrier is only 6 cm −1 (1.2 × 10 −22 J or 72 J mol −1).