Phosphorus substituted hydroxylamine and hydroxamic acid derivatives: synthesis and reactivity

Abstract

Dedicated to Prof. Julio Alvarez-Builla on the occasion of his 65 th anniversary AbstractThis review summarizes several reports concerning the synthesis and synthetic applications of hydroxylamines derived from phosphines, phosphine oxides and phosphonates, and phosphorus substituted hydroxamic acid derivatives. The first section outlines the synthesis and reactivity of phosphorus O-substituted and N-substituted hydroxylamines as well as several transformations of phosphorus substituted hydroxylamines including: rearrangement, hydrolysis, reduction and oxidation reactions. The second part of the review covers the synthesis and reactivity of phosphorus O-, N-, and C-substituted hydroxamic acid derivatives.

Synthesis of 1,3-Aminoalcohols and Spirocyclic Azetidines via Tandem Hydroxymethylation and Aminomethylation Reaction of β-Keto Phosphonates with N-Nosyl-O-(2-bromoethyl)hydroxylamine

“…On the other hand, hydroxylamines characterized by a weak N−O bond within the structure are commonly used reagents in organic synthesis. 4 Conventionally, they were extensively exploited as amination reagent in transition metal-catalyzed C−N bond-forming reactions. 5 In recent years, they have also been exploited as nitrogencentered radical precursors in photocatalytic C−N bondforming reactions 6 (Scheme 1B).…”