Selective functionalization and preorganization of calix[8]arenes

New Journal of Chemistry

Volumn 20, Issue 4, 1996, Pages 433-446

  Neri, Placido ^a   Consoli, Grazia M L ^a   Cunsolo, Francesca ^a   Geraci, Corrada ^a   Piattelli, Mario ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000931019     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (63)

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39. Muthukrishnan R., Gutsche C. D., J. Org. Chem., 1979, 44, 3962-3964.
40. In the formulas 4-7 the unknown substitution pattern is evidenced by a zigzag bond between the two kind of aromatic rings.
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51. Other factors such as "solubility" and "steric crowding" could be taken in consideration for a full explanation of alternate alkylation mechanism.
52. Cunsolo F., Piattelli M., Neri P., J. Chem. Soc., Chem. Commun. 1994, 1917-1918.
53. Crowned calix[4]arenes have been recently reviewed (Asfari Z., Wenger S., Vicens J., J. Incl. Phenom., 1994, 19, 137-148.
54. See also: Casnati A., Pochini A., Ungaro R., Ugozzoli F., Arnaud F., Fanni S., Schwing M.-J., Egberink R. J. M., de Jong F., Reinhoudt D. N., J. Am. Chem. Soc., 1995, 117, 2767-2777 and references cited therein).
55. The first examples of calix[5]crowns and calix[6]crowns were reported in (Kraft D., Arnecke R., Böhmer V., Vogt W., Tetrahedron 1993, 49, 6019-6024)
56. and in (Casnati A., Jacopozzi P., Pochini A., Ugozzoli F., Cacciapaglia R., Mandolini L., Ungaro R., Tetrahedron, 1995, 51, 591-598), respectively.
57. Geraci C., Piattelli M., Neri P., Tetrahedron Lett., 1995, 36, 5429-5432.
58. Chawla H. M., Srinivas K., J. Chem. Soc., Chem. Commun., 1994, 2593-2594.
59. Chawla H. M., Srinivas K., Tetrahedron Lett., 1994, 35, 2925-2928.
60. Chawla H. M., personal communication.
61. Arduini A., Pochini A., Secchi A., Ungaro R., J. Chem. Soc., Chem. Commun., 1995, 879-880.
62. These procedures are very similar to that proposed for p-tert-butylcalix[8]arene (Munch J. H., Gutsche C. D., Org. Synth., 1989, 68, 243-246), since under these conditions many p-substituted phenols give the corresponding p-substituted calix[8]arenes.
63. See, for example: Lubitov I. E., Shokova E. A., Kovalev V. V., Synlett., 1993, 647-648.