Selective Aromatic N-Substitution with N-(4-Tolyl)hydroxylamine by Addition of Polar Aprotic or Diethereal Solvent

European Journal of Organic Chemistry

Volumn , Issue 20, 2003, Pages 3920-3922

  Takeuchi, Hiroshi ^a   Tateiwa, Jun Ichi ^a   Hata, Suguru ^a   Tsutsumi, Keisuke ^a   Osaki, Yoshinori ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

Amination; Amines; Aromatic substitution; Regioselectivity; Solvent effects

Indexed keywords

AMINE; ANISOLE; DIARYLAMINE; HYDROXYLAMINE; N (4 TOLYL)HYDROXYLAMINE; SOLVENT; TOLUENE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ATOM; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELECTRIC CONSTANT; ELECTRON; POLARIZATION; STEREOCHEMISTRY;

EID: 0242291966     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200200576     Document Type: Article

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19. 4 and concentrated under reduced pressure. The resulting oil was analyzed by GLC to determine the yields of N-(4′-tolyl)-2- and -4-anisidines (3a), 2-amino-2′- and -4′-methoxy-5-methylbiphenyls (4a) and 4,4′-dimethylazoxybenzene (5). GLC yield: 3a 72% (2-anisidine/4-anisidine = 9:91); 4a 0%; 5 25%. The oil was subjected to silica gel column chromatography with hexane and hexane/ethyl acetate as eluents to provide 3a (129.0 mg, 60%, 2-anisidine/4-anisidine = 0:100) and a mixture of 3a (2-anisidine/4-anisidine = 100:0) and 5 (18.1 mg, GLC ratio 3a/5 = 62:38).