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tert-Butyloxycarbonyl protecting group. The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group [1] (BOC group) is an acid-labile protecting group used in organic synthesis. The BOC group can be added to amines under aqueous conditions using di-tert-butyl dicarbonate in the presence of a base such as sodium hydroxide:
Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. [1] Since this compound can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl (Boc) group, it is commonly referred to as Boc anhydride. This pyrocarbonate reacts with amines to give N-tert-butoxycarbonyl or so-called Boc
The tert-butyloxycarbonyl group is marked blue. Amines have a special importance in peptide synthesis, but are a quite potent nucleophile and also relatively strong bases. These characteristics imply that new protecting groups for amines are always under development. [47] Amine groups are primarily protected through acylation, typically as a ...
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.
Tert-Butylamine; Butylated hydroxyanisole; Butylated hydroxytoluene; 4-tert-Butylbenzaldehyde; N-tert-Butylbenzenesulfinimidoyl chloride; Para-tert-Butylbenzoic acid; 4-tert-Butylcatechol; Tert-Butyldiphenylsilyl; Tert-Butylhydroquinone; Tert-Butyllithium; Tert-Butyloxycarbonyl protecting group; Tert-Butylphosphaacetylene; Tert-Butylthiol; N-t ...
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Gelators serve as stabilizers and thickeners, thickening the gel solution while simultaneously maintaining the gel’s flexible nature. [8] When dispersed through the solvent as a colloid, gelators offer a stable internal structure to the gel. [8] Gelators are usually chosen based on their affinity for the solvent and the purpose of the gel. [5]
Heating the product at 60 °C for 3 hours causes the expulsion of a di-tert-butylacetylene and the reformation of P-P bonds. Another reaction pathway involves the addition of 3 equivalents of CO to the product, leading to the production of Ni(IMes)(CO) 3 and the ladderane-like compound described at the beginning of this section.