The selective protection and deprotection of ambident nucleophiles with parent and substituted triarylmethyls

Demirtaş İ., Büyükkidan B., Elmastaş M.

Turkish Journal of Chemistry, vol.26, no.6, pp.889-896, 2002 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 26 Issue: 6
  • Publication Date: 2002
  • Journal Name: Turkish Journal of Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.889-896
  • Keywords: 4,4'-dimethoxytriphenylmethyl chloride and selective protection, Aminophenols, Triphenylmethyl chloride
  • Ondokuz Mayıs University Affiliated: No

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'-dimethoxytriphenylmethyl chloride. S-triphenylmcthyl-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.