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Triphenylmethyl chloride is commercially available. It may be prepared by the reaction of triphenylmethanol with acetyl chloride, or by the Friedel–Crafts alkylation of benzene with carbon tetrachloride to give the trityl chloride-aluminium chloride adduct, which is then hydrolyzed. [3]
The triphenylmethyl substituent, also called trityl after 1927 suggestion by Helferich et al. [7], is widely used in organic chemistry. Trityl serves as a protecting group for alcohols. [8] protection (requires proton acceptor): Ph 3 CCl + ROH → Ph 3 COR + HCl deprotection: Ph 3 COR + HBr → ROH + Ph 3 CBr
The presence of three adjacent phenyl groups confers special properties manifested in the reactivity of the alcohol. For example it reacts with acetyl chloride, not to give the ester, but triphenylmethyl chloride: [5] Ph 3 COH + MeCOCl → Ph 3 CCl + MeCO 2 H. The three phenyl groups also offer steric protection.
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The triphenylmethyl radical can be prepared by homolysis of triphenylmethyl chloride 1 by a metal like silver or zinc in benzene or diethyl ether. The radical 2 forms a chemical equilibrium with the quinoid-type dimer 3 (Gomberg's dimer). In benzene the concentration of the radical is 2%. [3] Triphenylmethyl radical
It is the thiol derivative of the bulky substituent triphenylmethyl (called trityl). [1] [2] The compound forms a number of unusual derivatives that are more stable than less bulky analogues. The sulfenyl chloride (C 6 H 5) 3 CSCl is obtained from the thiol with sulfuryl chloride. It in turn reacts with ammonia to form the sulfenamide (C 6 H 5 ...
Gomberg radical reaction, forming a triphenylmethyl radical by treating triphenylmethyl chloride with certain metals; See also. Moses Gomberg (1866–1947), ...
The very stable triphenylmethyl carbocation derived from solvolysis of the corresponding triphenylmethyl chloride reacts 100 times faster with the azide anion than with water. When the carbocation is the very reactive tertiary adamantane carbocation (as judged from diminished rate of solvolysis) this difference is only a factor of 10.