Selective derivatization of calix[4]arenes via amino groups attached to the wide rim

Collection of Czechoslovak Chemical Communications

Volumn 69, Issue 5, 2004, Pages 1009-1026

  Bogdan, Anca ^a   Vysotsky, Myroslav O ^a   Böhmer, Volker ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Acylations; Amines; Anilines; Calixarenes; Hydrogenation; ipso Nitration; Nitro compounds; NMR spectroscopy; Regioselectivity

Indexed keywords

CALIXARENE; ETHER DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL REACTION; HYDROGENATION; NITRATION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 3242808139     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20041009     Document Type: Article

References (51)

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41. The preparation of the calix[4]arene/fullerene conjugate involves a 1,3-diacylation: Soi A., Hirsch A.: New J. Chem. 1998, 1337.
42. Partial ipso-nitration has been described first by Verboom W., Durie A., Egberink R. J. M., Asfari Z., Reinhoudt D. N.: J. Org. Chem. 1992, 57, 1313 for the tetrapropyl ether.
43. Probably for tetraethers with different ether residues, optimum conditions have to be worked out for the partial ipso-nitration, while the further reactions should be more or less general.
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48. Tetraurea derivatives with two different urea residues obtained by this method will be subject of a forthcoming article, see also: Pop A., Vysotsky M. O., Saadioui M., Böhmer V.: Chem. Commun. 2003, 1124.
49. This sequence was used during the synthesis of selectively functionalized 1,3-alternate calix[4]arenes: Danila C., Bolte M., Böhmer V.: Unpublished results.
50. For the synthesis of derivatives with different ether residues the same comparison can be made: a) debutylation (66-75%); b) 1,3-di-O-alkylation (96%); c) selective nitration of the phenolic units (65%); d) 2,4-di-O-alkylation (98% in the case of methylation); e) iodination (at 2,4 position 93%); f) substitution with potassium phthalimide (70%); overall yield 26-29% versus: a) 1,3-di-O-alkylation (96%); b) selective ipso-nitration of the phenolic units (76%); c) 2,4-di-O-alkylation (98% in the case of methylation); d) reduction of nitro groups; e) formation of phthalimides (d + e 82-92%); f) ipso-nitration (78-92%) overall 45-60%.
51. For mononitro derivatives see: Mogck O., Parzuchowski P., Nissinen M., Böhmer V., Rokicki G., Rissanen K.: Tetrahedron 1998, 54, 10053; for a general method of ipso-nitration see 24.