Regioselective Aromatic Nucleophilic Substitution in N-Aryl-2-nitrosoanilines with Oxygen and Nitrogen Nucleophiles

Autor:	Andrzej Kwast, Zbigniew Wróbel, Karolina Stachowska
Rok vydání:	2012
Předmět:	chemistry.chemical_compound chemistry Nucleophile Nucleophilic aromatic substitution Aryl Organic Chemistry Halogen Alkoxide Nucleophilic substitution Regioselectivity Nitroso Medicinal chemistry Catalysis
Zdroj:	Synthesis. 45:127-133
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0032-1316823
Popis:	Aromatic nucleophilic substitution of halogens in N-aryl-2-nitrosoanilines with ammonia, alkylamines and alkoxide ions proceeds efficiently and highly regioselectively in the position para to the nitroso group. When two halogen atoms ortho and para are present, the latter is substituted exclusively. Oxidative substitution of hydrogen at the unsubstituted ortho position of the nitrosoaniline ring does not compete with substitution of para halogen atoms. The reaction allows the synthesis of N-aryl-2-nitrosoanilines which cannot be obtained according to known methods.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a7bb0c3955fbb42bd8d239d0259fa783 https://doi.org/10.1055/s-0032-1316823 Zobrazit plný text záznamu