Photoacid generators (PAGs) based on N-acyl- N-phenylhydroxylamines for carboxylic and sulfonic acids

• Published in: Tetrahedron Vol. 67; no. 20; pp. 3733 - 3742
• Main Authors: Ikbal, Mohammed, Jana, Avijit, Singh, N.D. Pradeep, Banerjee, Rakesh, Dhara, Dibakar
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 20-05-2011; Elsevier
• Subjects: Bearing; Carboxylic acid; Carboxylic acids; Chemistry; Exact sciences and technology; Generators; Homolytic cleavage; Irradiation; N-Acyl- N-phenylhydroxylamine; Noncondensed benzenic compounds; Organic chemistry; Photoacid generator; Preparations and properties; Sulfonic acid; Tetrahedrons; N-Acyl- N-phenylhydroxylamine; Homolytic cleavage; Carboxylic acid; Sulfonic acid; Photoacid generator; Chemical rearrangement; Hydroxylamine; Polymer; N-Acyl-N-phenylhydroxylamine; Ketone; Ultraviolet radiation; Carboxylate; Irradiation; Benzenic compound; Aromatic compound; Homolysis; Aqueous solution; Chemical synthesis; Methanol
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.03.049

Simple and efficient photoacid generators (PAGs) for carboxylic and sulfonic acids based on
N-acyl-
N-phenylhydroxylamines have been demonstrated. Irradiation of
o-carboxylates and thermally rearranged
o-arenesulfonates of
N-acyl-
N-phenylhydroxylamines using UV light (≥254 nm) in aqueous methanolic solution resulted in efficient generation of carboxylic and sulfonic acids, respectively. The carboxylic acid generation ability of
N-acyl-
N-phenylhydroxylamines was found to be dependent on their
N-acyl substituents. Further, polymer bearing
o-arenesulfonates of
N-acyl-
N-phenylhydroxylamine was synthesized and demonstrated as PAG for sulfonic acids.
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