Abstract
A study of the Mitsunobu reaction involving calix[4]arene and a series of benzylic and allylic alcohols reveals the structural effect of the alcohol component on the distribution between Oand C-alkylation of the phenol component in the formation of aryl alkyl ethers and p-alkylated phenols, respectively.
Similar content being viewed by others
REFERENCES
Paper 56 in a series entitled “Calixarenes.” For paper 55, see wang, J.; Bodige, S. G.; Watson, W. H.; Gutsche, C. D. J. Org. Chem. 2000, 65, 8260.
(a) Wang, J.; Gutsche, C. D. J. Amer. Chem. Soc. 1998, 120, 12226; (b) Gibbs, C. G.; Wang, J., Gutsche, C. D. in Calixarenes for Separations; ACS Symp. Ser. 757, Lumetta, G. J.; Rogers, R. D. and Gopalan, A. S. Eds.; 2000; p. 313; (c) Wang, J.; Gutsche, C. D. J. Org. Chem. 2000, 65, 6273; (d) Wang, J.; Bodige, S. G.; Watson, W. H.; Gutsche, C. D. J. Org. Chem. 2000, 65, 8260.
Mitsunobu, O. and Yamada, M. Bull. Chem. Soc., Jpn. 1967, 40, 2380.
(a) Mitsunobu, O. Synthesis 1981, p. 1; (b) Hughes, D. L. Org. Reaction, 1992, 42, 335; (c) Hughes, D. L. Org. Prep. Proceed. Intern. 1996, 28, 127.
For general reviews of calixarene chemistry, see the following reviews: (a) Gutsche, C. D. Calixarenes Revisited In Monographs in Supramolecular Chemistry; Stoddart, J. F. Ed., Royal Society of Chemistry, London, 1998; (b) Böhmer, V., Angew. Chem. Intern. Ed. Engl. 1995, 34, 713-745; (c) Gutsche, C. D. Aldrichim. Acta, 1995, 28, 3-9; (d), Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens, J.; Bohmer, V. Eds. Kluwer, Dordrecht, 1991; (e) Gutsche, C. D. Calixarenes In Monographs in Supramolecular Chemistry, Stoddart, J. F. Ed., Royal Society of Chemistry, London, 1989.
(a) Dondoni, A.; Marra, A.; Scherrmann, M.-C.; Casnati, A.; Sansone, F. and Ungaro, R. Chem. Eur. J. 1997, 3, 1774; (b) Marra, A.; Scherrmann, M.-C.; Dondoni, A.; Casnati, A.; Minari, P.; and Ungaro, R. Angw. Chem. Intern. Ed. Engl. 1994, 33, 2479.
Arduini, A.; Pochini, A.; Rizzi, A.; Sicuri, A. R.; Ugozzoli, F.; Ungaro, R. Tetrahedron 1992, 48, 905.
Le Noble, W. J. Synthesis 1970, p. 1.
Danishefsky, S.; Berman, E. M.; Ciufolini, M.; Etheredge, S. J.; Segmuller, B. E., J. Amer. Chem. Soc. 1985, 107, 3891.
(a) Sharma, S. K.; Gutsche, C. D. J. Org. Chem. 1996, 61, 2564, (b) van Loon, J.-D.; Arduini, A.; Verboom, W.; Ungaro, R.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. Tetrahedron Lett. 1989, 30, 2681; (c) van Loon, J.-D.; Arduini, A.; Coppi, L.; Verboom, W.; Pochini, A.; Ungaro, R.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639.
Wang, J.; Mendez-Rojas, M.; Bodige, S. G.; Watson, W. H.; Gutsche, C. D. unpublished observation.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Wang, J., Gutsche, C.D. Structural Effects in the Mitsunobu Reaction of Calix[4]arene with Benzylic and Allylic Alcohols [1]. Structural Chemistry 12, 267–274 (2001). https://doi.org/10.1023/A:1016624410259
Issue Date:
DOI: https://doi.org/10.1023/A:1016624410259