O-(Diphenylphosphinyl)hydroxylamine

Introduction

Electrophilic amination gains more and more importance with the increasing interest in primary amines. Indeed they are valuable as synthetic intermediates or entries into nitrogen-containing heterocyclic systems. Moreover, electrophilic amination allows a direct metal-free access to hydrazines.

To perform electrophilic amination, activated hydroxyl­amines are the most common kind of reagents used. [1] Lots of such hydroxylamines exist, but O-(diphenylphosphinyl)hydroxylamine (1) presents many advantages. In fact, it has the most extensive track record for amination. [2] Compared to other activated hydroxylamines, the diphen­ylphosphinyl reagent has the best reputation for stability: The solid compound may be stored for long periods at 0 °C and does not show any degradation when employed below 140 °C. [3] It presents only a low tendency toward side reactions and supports strong bases like lithium diisopropylamide or butyllithium. [1]

Compound 1 is not commercially available but it can be readily and rapidly prepared in a one-step reaction from diphenylphosphonic chloride and hydroxylamine. [4]

Scheme 1

References

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