1010101-59-3

Upstream product

• 1010101-50-4 N-Boc-N-(4-tolyl)-O-tetrahydropyranylhydroxylamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 623-10-9 N-(4-methylphenyl)hydroxylamine 

Downstream Products

• 1095280-72-0 N-Boc-N-(4-methylphenyl)-O-(4-nitrobenzoyl)hydroxylamine 
• 1095280-81-1 2-(Boc-amino)-5-methylphenyl methanesulfonate 
• 1218786-39-0 N-Boc-2-(2',2',2'-trichloroacetylamino)-4-methylaniline 
• 328267-64-7 (2-hydroxy-4-methylphenyl)carbamic acid tert-butyl ester 
• 1448755-16-5 C₂₀H₂₅NO₂ 

Relevant academic research and scientific papers

Copper-catalyzed coupling of hydroxylamines with aryl iodides

An efficient method for the copper-catalyzed N-arylation of hydroxylamines with aryl iodides is described. A variety of N- and O-functionalized hydroxylamines were transformed in good to excellent yield with a broad range of aryl coupling partners. Methods for the selective deprotection of either the N- or O-substituents for further functionalization are also described.

Rearrangement of differentially protected N-arylhydroxylamines

The rearrangement of a series of N,O-difunctionalised N-arylhydroxylamines to generate protected 2-aminophenols has been investigated. N-Boc-N-Aryl-O- acylhydroxylamines are stable, isolable compounds which rearrange smoothly at temperatures between 110 and 140°C. The corresponding N-Boc-N-aryl-O- sulfonylhydroxylamines were not isolated and rearrange to 1,2-difunctionalised aminophenols at room temperature in excellent yield. Deprotection of either the N- or O-substituents under standard conditions allows for further synthetic manipulation of either the aniline or phenol functionality. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.