DOI: 10.1039/A706018A
(Paper)
Reference Section for: Chem. Commun., 1998, 9-10
Calix[4]pyridine: a new arrival in the heterocalixarene family
(Note: The full text of this document is currently only available in the PDF Version )
Vladimír Král, Philip A. Gale, Pavel Anzenbacher Jr., Karolina Jursíková, Vincent Lynch, Jonathan L. Sessler, Vladimír Král and Pavel Anzenbacher Jr.
Abstract
Reaction of dichlorocarbene with meso-octamethylcalix[4]pyrrole causes pyrrole ring expansion, producing chlorocalixpyridinopyrroles and chlorocalixpyridines.
References
- For an early review of pyridine containing macrocycles (along with furan and thiophene) see G. R. Newkome, J. D. Sauer, J. M. Roper and D. C. Hager, Chem. Rev., 1977, 77, 513 Search PubMed . Mixed porphyrin-like pyrrole-pyridine systems are also known; see for instance T. D. Lash and S. T. Chaney, Chem. Eur. J., 1996, 2, 944 CrossRef CAS; T. Schönemeier and E. Breitmaier, Synthesis, 1977, 273 Search PubMed . For dodecahydrohexaazakekulene synthesis see H. A. Staab and F. Diederich, Chem. Ber., 1983, 116, 3487 CrossRef CAS; H. A. Staab, F. Diederich, C. Krieger and D. Schweitzer, Chem. Ber., 1983, 116, 3504 . For the synthesis of sexipyridines, see J. L. Toner, Tetrahedron Lett., 1983, 24, 2707 Search PubMed; G. R. Newkome and H.-W. Lee, J. Am. Chem. Soc., 1983, 105, 5956 CAS.
- For a review of homocalixarenes and homocalixpyridines, see G. Brodesser and F. Vögtle, J. Inclusion Phenom., 1994, 19, 111 Search PubMed.
- G. R. Newkome, Y. J. Joo and F. R. Fronczek, J. Chem. Soc., Chem. Commun., 1987, 854 RSC.
- D. Jacoby, S. Isoz, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1995, 117, 2793 CrossRef CAS.
- C. D. Gutsche and M. Iqbal, Org. Synth., 1990, 68, 234 CAS.
- A. Bayer, Ber. Dtsch. Chem. Ges., 1886, 19, 2184 Search PubMed; D. Jacoby, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Chem. Soc., Chem. Commun., 1991, 220 RSC; P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140 CrossRef CAS; P. A. Gale, J. L. Sessler, V. Lynch and P. I. Sansom, Tetrahedron Lett., 1996, 37, 7881 CrossRef CAS; W. E. Allen, P. A. Gale, C. T. Brown, V. M. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1995, 118, 12 471 CrossRef; J. L. Sessler, A. Andrievsky, P. A. Gale and V. Lynch, Angew. Chem., Int. Ed. Engl., 1996, 35, 2782 CrossRef CAS; P. A. Gale, J. L. Sessler, W. E. Allen, N. A. Tvermoes and V. Lynch, Chem. Commun., 1997, 665 RSC.
- C. W. Rees and C. E. Smithen, J. Chem. Soc., 1964, 928 RSC; C. W. Rees and C. E. Smithen, J. Chem. Soc., 1964, 938 RSC; R. L. Jones and C. W. Rees, J. Chem. Soc. (C), 1969, 2249 RSC; R. L. Jones and C. W. Rees, J. Chem. Soc. (C), 1969, 2251 RSC; R. L. Jones and C. W. Rees, J. Chem. Soc. (C), 1969, 2255 RSC.