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tert-Butyl chloride is the organochloride with the formula (CH 3) 3 CCl. It is a colorless, flammable liquid. It is sparingly soluble in water, with a tendency to undergo hydrolysis to the corresponding tert-butyl alcohol. It is produced industrially as a precursor to other organic compounds. [1]
N-tert-Butylbenzenesulfinimidoyl chloride is a useful oxidant for organic synthesis reactions. [1] It is a good electrophile, and the sulfimide S=N bond can be attacked by nucleophiles, such as alkoxides, enolates, and amide ions. The nitrogen atom in the resulting intermediate is basic, and can abstract an α-hydrogen to create a new double bond.
The tert-butoxide is a strong, non-nucleophilic base in organic chemistry. It readily abstracts acidic protons from substrates, but its steric bulk inhibits the group from participating in nucleophilic substitution, such as in a Williamson ether synthesis or an S N 2 reaction. tert-Butyl alcohol reacts with hydrogen chloride to form tert-butyl ...
The addition of tri-tert-butyl cyclopropenium ion produces the thermally stable cyclopropenyl phosphine intermediate. Upon irradiation with 254 nm light in the presence of triflic acid and either tetra- n -butyl ammonium chloride or tetramethylammonium fluoride , the anthracene leaving group is forced out, leaving a halogenated phosphine.
The effect of the tert-butyl group on the progress of a chemical reaction is called the Thorpe–Ingold effect illustrated in the Diels-Alder reaction below. Compared to a hydrogen substituent, the tert-butyl substituent accelerates the reaction rate by a factor of 240. [2] tert-Butyl effect. The tert-butyl effect is an example of steric hindrance.
Tetrabutylammonium chloride is the organic compound with the formula [(CH 3 CH 2 CH 2 CH 2) 4 N] + Cl −, often abbreviated as [Bu 4 N]Cl, where Bu stands for n-butyl. A white water-soluble solid, it is a quaternary ammonium salt of chloride. It is a precursor to other tetrabutylammonium salts.
Tetrabutyltin is the organotin compound with the molecular formula Sn(CH 2 CH 2 CH 2 CH 3) 4 or SnBu 4, where Bu is butyl −CH 2 CH 2 CH 2 CH 3. Sometimes abbreviated TTBT, it is a colorless, lipophilic oil. [3] Tetrabutyltin is a precursor to tributyltin and dibutyltin compounds.
Industrial preparation of organolithium reagents is achieved using this method by treating the alkyl chloride with metal lithium containing 0.5–2% sodium. The conversion is highly exothermic. The sodium initiates the radical pathway and increases the rate. [60] The reduction proceeds via a radical pathway.