Hydroxylamine o-sulfonic add

In the presence of a base, hydroxylamine-O-sulfonic add or chloramine aminate carbonyl compounds nucleophihcally, for example ... 

The action of ammonia or primary amines and hydroxylamine-O-sulfonic add upon ketones also yields diaziridines. Likewise, the amination of imines (azomethines) with hydroxylamine-O-sulfonic acid yields diaziridines ... 

A. Citterio, A. Gentile, F. Minisci, M. Serravalle, S. Ventura, Polar effects in free-radical reactions. Carbamoylation and a-N-amidoalkylation of heteroaromatic bases by amides and hydroxylamine-O-sulfonic add, J. Org. Chem. 49 (1984) 3364-3367. 

Hydroxylamine-O-sulfonic acid for N-amination of pyridine, 43, 1 Hydroxylation of indene, 41, 53 2-Hydroxy-3-methylbenzoic add, oxidation to 2-hydroxyisophthalic acid by lead dioxide, 40, 48 Rydroxymethyleerrocene. 40, 52... 

The action of methanolic sodium methoxide on hydroxylamine O-sulfonic acid generates nitrene NH, which adds to butadiene in situ to give a low yield of l//-pyrroline 295 (equation 154)146. 

The reaction is reversible, but the state of equilibrium highly favors the desired products. Preparations of large quantities for synthetic work are illustrated for methyl ethyl ketoxime, cyclohexanone oxime, hept-aldoxime, and benzophenone oxime, the procedures varying somewhat with the nature of the carbonyl compound. In some instances, a readily available and cheap reagent like sodium hydroxylamine disulfonate, HON(SO,Na)j, is first prepared from sodium nitrite and sodium bisulfite and, without isolation, treated with the carbonyl compound, Hydioxylamine-O sulfonic add, Ii,NOSO,H, is still another reagent and, like sodium hydroxylamine disulfonate, is used in the absence of a base. The preparation of hydroxylamine hydrochloride is described. ... 

The capacity of hydroxylamines derivatives to be either O- or N-nucleophiles in the reactions with acetylene compounds often depends even upon the structure of the latter. For example, N-t-butylhydroxylamine can add to acetylenic sulfones through nitrogen or oxygen atom depending on the character of the second radical at the triple bond (Scheme 1.201) [406],... 

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