Sulfonyl hydroxylamines

This presumably forms oxime, 120, on reaction with hydroxylamine that intermediate is not isolated as it cyclizes spontaneously to the isoxazole, 121. Acylation of the isoxazole with the sulfonyl chloride, 88, affords sulfisoxazole (98) after removal of the acetyl group. 

O-Alkyl-7 und O-Aryl-hydroxylamine8 lassen sich mit Lithiumalanat in die Komponenten spalten bzw. re-duktivumlagern , O-Acyl-10bzw. N-Sulfonyl-hydroxylamine11 imerstenSchritt zum Hydroxylamin und Al-kohol bzw. Sulfonamid reduzieren. 

N-Diphenylmethylen- 374 N-Diphenylmethylen-O-aminocarbonyl- 612 N-[l,3-Diphenyl-propyl-(2) - 374 N-[l,3-Diphenyl-propyliden-(2)]- 374, 377, 380 N-(4-Halogen-phenyI)- 683 N-Heptyl- 375 N-Heptyl-N-acetyl- 376 N-Heptyliden- 375 N-Hcptyliden-O-acetyl- 376 0-(2-Hydroxy-athyl)-N-athoxycarbonyl- 133 N-(4-Hydroxy-phenyl)- 683 0-(2-Hydroxy-l-phenyl-athyI)-N-athoxycarbonyI-aus 0-(ci-AthoxycarbonyI-benzyl)-N-athoxycar-bonyl-hydroxylamin und Lithiumalanat 133 N-Isopropyl- 682 N-Isopropylidcn- 613 N-Methyl- 133, 682 O-Methyl-N-bcnzyliden- 377 O-Methyl-N-benzyliden- 375 0-Methyl-N-(4-chlor-benzyl)- 375 0-Methyl-N-(4-chlor-benzyliden)- 375 N-Methy -N,0-diacetyI- 682 N-(4-Methyl-phenyl)- 683 0-McthyI-N-( 1 -phenyl-athyliden)- 375 N-(4-Methylthio-phenyl)- 684 N-(4-Nitro-benzyl)- 374 N-[4-Nitro-benzyliden - 374, 377 N-(2-Nitro-phenyl)- 562 N-(4-Nitro-phenyl)- 682 N-Nitroso-N-cyclohexyl- 697 N-Octyl- 374 N-Octyl-(2)-N-acetyl- 376 N-Octyliden- 374 N-0ctyliden-(2)-0-acctyl- 376 N-(Pentafluor-phenyl)-0,N-diacetyl- 697 N-Phenyl- 474, 481, 682, 783 N-Phenylacetyl-O-benzoyl- 265 N-(l-Phenyl-athyl)- 374 N-(l-Phenyl-athyl)-N-acetyl- 376 N-(l-Phenyl-athyliden)-374, 613 N-( l-Phenyl-athyliden)-0-acetyl- 376 N-[ 1 -Phenyl-buten-( 1 )-yl-(3)-iden]- 582 N-f4-Phenyl-butyl-(2)-iden]- 581 N-Phcnyl-N,0-diacetyl- 682 N-(4-Phenylthio-phenyl)- 684 N-Propyl-N-cyclohexyl- 376 N-Propyl-N-isopropyl- 376 O-Sulfonyl- 481 N-(4-Sulfonyl-phenyI)- 683 N-(2-Vinyl-phenyl)- 698... 

Al-(Alkoxycarbonyl) 0-(arenesulfonyl)hydroxylamines [alkyl Af-(arenesulfonyloxy) carbamates] 3i-o can be easily obtained by sulfonylation of commercially available iV-(alkoxycarbonyl)hydroxylamines (alkyl V-hydroxy carbamates). Af-(Alkoxycarbonyl) hydroxylamines can be also prepared from hydroxylamine and alkyl chloroformate . ... 

Hoffman and coworkers have extensively studied the reactions between amines and sulfonyl peroxides. When primary amines reacted with arylsulfonyl peroxides at —78 °C in ethyl acetate, A-alkyl-O-arylsulfonyl hydroxylamine derivatives were obtained (equation 8), whereas when various primary and secondary amines reacted with sulfonyl peroxides, oxidative deamination was observed. ... 

Aminofuro[3,2- ]pyridinium tosylates can be prepared from furopyridines by treatment with 0-(4-methylbenzene-sulfonyl)hydroxylamine. Treatment of the tosylate salt with base, such as potassium carbonate, leads to a pyridinium A -imide, 50. Compound 50 readily undergoes 1,3-dipolar cycloaddition reactions <1999CCC539>. 

O-Mesitylenc sulfonylhydroxylamine Hydroxylamine, O-mesityl-sulfonyl- (8) Hydroxylamine, 0-[(2,4,6-trimethylphenyl)sulfonyl]-... 

This is very similar to the above method of conversion of pyridinium Ar-imides to 1,2-diazepines. Here the tetrahydrocarbolines <1996CHEC-II(9)113> or the tetrahydroisoquinolines <1984CHEC(7)593> are N-substituted and N-aminated with O-sulfonyl hydroxylamine derivatives followed by treatment with base to give the corresponding 1,2-diazepines. 

The amination of 5-phenyl-l,5-dihydro[l,2,3]triazolo[4,5- /]-l,2,3-triazole (31) with o-(mesityl-sulfonyl)hydroxylamine afforded two V-aminated products distinguishable on the basis of their l3C NMR spectra (Equation (1)). The major product (46%), showed one carbon signal other than those from the phenyl ring and was therefore assigned as the symmetrical 2-amino derivative (32). The minor product showed two l3C signals in addition to those from the phenyl ring and was believed to be represented by structure (33) or (34) (33) is the preferred isomer on the basis of the similarity of its NMR spectrum to that of known l-acetyl-5-phenyltriazolotriazole. 

Reduction of T [l-(2-nitrophenyl)-l//-pyrrol-2-yl]sulfonyl -acetone or -1-phenylethan-l-one with sodium borohy-dride and 5% palladium on carbon, a reagent known to convert aromatic nitro compounds to hydroxylamines, triggers intramolecular interaction and gives pyrrolo[l,2- ][3,l,6]benzothiadiazocine derivatives 90 (Equation 11 <2001MI1405, 2004T8807>). This method was further successfully applied to the reductive cyclization of 2- [l-(2-nitrophenyl)-17/-pyrrol-2-yl]sulfanyl acetonitrile. 

Hydroxylamin 0-[4-Nitro-3-(phenyl-sulfonyl-methyl)-phenyl]- E16a, 253 (N-Deacylier.)... 

C7H803 ethyl maltol 4940-11-8 474.75 41.463 2 11021 C7H9N03S o-4-toluene sulfonyl hydroxylamine 52913-14-1 773.15 70.660 2... 

The nucleophilic addition of lithiated allyl phenyl sulfone to nitrones at 0 °C afforded 4-(phenylsulfonyl)isoxazol-idines as major products. The process probably involves the isomerization of the allylsulfonyl moiety of the initially formed hydroxylamine anion to vinylsulfone which then undergoes intramolecular Michael addition. For example, the chiral nitrone 536 afforded isoxazolidine 537 with high diastereoselectivity (Equation 88) <2005T3335>. When the same reaction was carried out in the presence of hexamethylphosphoramide (HMPA) at —80°C, the anti-a-sulfonyl homoallyl hydroxylamine was obtained. 

Generally sulfonyl esters of serine are relatively stable with respect to reactivation by a nucleophile such as hydroxylamine (Alexander et al. 1963). However, treatment of the sulfonyl derivatives of chymotrypsin with 0.1 N NaOH at 0°C yields a dehydroalanine residue in... 

Electron-deficient alkenes (e.g., NCHC=C(COOMe)2) can be aziridinated with 0-(aryl-sulfonyl)hydroxylamines <9lCOS(7)469>. The reaction is believed to involve a Michael addition followed by cyclization with expulsion of a sulfonate anion. Less electrophilic alkenes react in lower yield but with high stereoselectivity (Equation (2)). The chiral catalyst prepared from an optically active bisoxazoline and Cu(I)triflate is effective in promoting the enantioselective aziridination of alkenes <93JA5328>. The addition of nitrosyl chloride to alkenes, which are especially susceptible to... 

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