Hydroxylamine-O-sulfonic Acid

Kinetic study of the amination of Grignard reagents and cuprates with O‐methylhydroxylamine

“…For the amination of higher order lithium cuprates with 6, Casarinl et al offered a mechanism which is in accordance with Beak et al's approach. 18 The crystal structure of N-lithio-N-(tert-butoxycarbonyl)-O-tosylhydroxylamine (7) was reported by Boche et al 19 Stimulated by our work on the competitive kinetic study of the amination of phenyl carbanions with acetone O-(2,4,6-trimethylphenylsulfonyl)oxime (9) (R 1 ¼ C 6 H 2 Me 3 -2,4,6), 20 we tried to find kinetic support for the polar S N 2-like mechanism for the amination of carbanions with 1.…”

Direct and Stereospecific Synthesis of N‐H and N‐Alkyl Aziridines from Unactivated Olefins Using Hydroxylamine‐O‐Sulfonic Acids

“…[8] However, no aziridination products were detected. After a thorough literature survey of inexpensive yet powerful aminating agents, we noted that hydroxylamine- O -sulfonic acid (HOSA) [9] has the potential to be the optimal reagent for our purposes: (a) HOSA has been widely used for the synthesis of amines, as well as for the preparation of nitriles, oximes, amides and various nitrogen-containing heterocycles; [10] (b) HOSA does not contain a nitro group and it has robust thermal stability (decomposition temperature: 208–211 °C) and is a widely available and cost-effective commercial source of electrophilic nitrogen; (c) the byproduct derived from HOSA is an inorganic sulfate after workup, which can be conveniently removed by simple aqueous extraction. Among publications focused on HOSA, several reports on olefin hydroamination drew our attention.…”