The Selective Protection and Deprotection of Ambident Nucleophiles with Parent and Substituted Triarylmethyls

Authors: İBRAHİM DEMİRTAŞ, BÜLENT BÜYÜKKIDAN, MAHFUZ ELMASTAŞ

Abstract: N-triphenylmethyl and N-4,4'-dimethoxytriphenylmethyl of o-aminophenol, m-aminophenol, and p-aminophenol compounds were easily prepared from triphenylmethyl chloride and 4,4'-dimethoxytriphenyl- methyl chloride. S-triphenylmethyl-2-mercapto ethanol was also selectively synthesized using the triphenylmethyl chloride and 2-mercapto ethanol. The reactivity of nitrogen and sulfur versus oxygen in the protection reactions was compared. In principle, the protection of aminophenols and 2-mercapto ethanol with triarylmethyls (trityls) may take place on the oxygen. However, in this framework, we discuss the different reactivities of oxygen, nitrogen and sulfur towards triphenylmethyl chloride (TrCl) and 4,4'-dimethoxytriphenylmethyl chloride (DMTrCl) and find that nitrogen and sulfur are more reactive than oxygen.

Keywords: The Selective Protection and Deprotection of Ambident Nucleophiles with Parent and Substituted Triarylmethyls

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