Intramolecular imine cross-coupling in dibenzylidine sulfamides: Synthesis of unsymmetrical 1,2-diaryl ethanediamines

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2859-2862

  Pansare, Sunil V ^a   Malusare, Mahesh G ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE; ETHYLENEDIAMINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029983326     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00406-6     Document Type: Article

References (30)

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16. 1 = Ph, 1.52 g, 80%) which was used further without purification.
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23. 3).
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29. This is a modification of a procedure for the cleavage of benzenesulfonamides, see: Snyder, H, R.; Heckert, R. E. J. Am. Chem. Soc. 1952, 74, 2006-2009.
30. Coupling of symmetrical 2 derived from 2-methyl benzaldehyde gives cis 3 as the major product (cis/trans = 5/1). This result is contrasteric and a simple explanation is not apparent. Stereoselectivity in intramolecular reductive coupling of symmetrical diimines leading to macrocycles is reported to depend on the electronic nature of the aryl group (trans/cis ratio is higher with p-electron donating substituents, see ref. 7.). No distinct electronic effects are seen in the present study.