Synthesis of functionalized oxacalix[4]arenes

Organic Letters

Volumn 7, Issue 1, 2005, Pages 91-94

  Katz, Jeffrey L ^a   Feldman, Michael B ^a   Conry, Rebecca R ^a  

^a Health Services and Department of Biology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; BENZENE DERIVATIVE; CALIXARENE; HYDROXYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 12344257153     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047840t     Document Type: Article

References (29)

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2. See: (a) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: London, 2000 and references therein. (b) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745 and references therein.
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18. 3 led to a very sluggish reaction, requiring 6-12 h for complete conversion.
19. NAr-based formation of tetranitroresorcinarenes using electrophile 1 proceeds at room temperature in DMF: Shivanyuk, A.; Far, A. R.; Rebek, J., Jr. Org. Lett. 2002, 4, 1555-1558.
20. 6b reported similar observations regarding reaction tolerance with respect to moisture, atmospheric oxygen, and concentration.
21. 4, filtered, and concentrated in vacuo. Purification is effected as described in Supporting Information.
22. For a discussion of the calixarene numbering scheme, see ref 1, section 1.4.
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24. The oxacalixarene X-ray structure reported by Chambers (ref 8) bore nitrogen atoms at the interior positions of the electrophilic component aromatic rings and adopted a 1,3-alternate conformation in the solid-state.
25. The 1,3-alternate conformation was also proposed for analogous thiacalix[4]arenes: Montaudo, G.; Bottino, F.; Trivellone, E. J. Org. Chem. 1972, 37, 504-505.
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