Effect of Substituents and Stability of Transient Aluminum–Aminals­ in the Presence of Nucleophiles

Abstract

Disubstituted hydroxylamines were synthesized and used to form aluminum–amide complexes. These reagents masked carbonyl groups in situ from nucleophilic addition. The stability and utility of the aluminum–aminals are presented in the context of selectively controlling nucleophilic addition on substrates with multiple carbonyl groups.

Selective Detection of Toxic C1 Chemicals Using a Hydroxylamine-Based Chemiresistive Sensor Array

“…MHAs were synthesized in two steps according to a literature procedure. , Potassium carbonate (1 equiv) was added to a solution of N -hydroxy-phthalimide (1.1 equiv) in DMSO, followed by stirring for 5 min. The required benzyl bromide or chloride (1 equiv) was then added to the solution, and the resulting mixture was stirred for 24 h at room temperature.…”