Syntheses, structures, and reactivity of 2,5-diboryl-1-alkylpyrroles and Di(1-alkyl-2-pyrrolyl)boranes

European Journal of Inorganic Chemistry

Volumn , Issue 3, 1999, Pages 399-404

  Faderl, Jürgen ^a   Deobald, Bernd ^a,b   Guilard, Roger ^b   Pritzkow, Hans ^a   Sichert, Walter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

1 Alkylpyrroles; Boranes; Lithiation; Porphyrinogenes; Tin boron exchange

Indexed keywords

BORON COMPOUNDS; HYDRIDES; TIN;

1-ALKYLPYRROLE; ALKYLPYRROLES; ARYLOXY; BORANE; LITHIATION; PORPHYRINOGENE; PYRROLYL; STRUCTURE ANALYSIS; TIN-BORON EXCHANGE; X-RAY STRUCTURE;

BORON;

BORANE DERIVATIVE; PYRROLE DERIVATIVE; TIN;

ARTICLE; CRYSTAL STRUCTURE; DERIVATIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 0032866528     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0682(199903)1999:3<399::aid-ejic399>3.0.co;2-i     Document Type: Article

References (35)

1. R. B. Woodward, Angew. Chem. 1960, 72, 651-662.
2. K. M. Smith in Comprehensive Heterocyclic Chemistry Vol. 4 (Ed.: A. R. Katritzky, C. W. Rees), Pergamon Press Oxford 1984, 378-419.
3. M. Pohl, H. Schmickler, J. Lex, E. Vogel, Angew. Chem. 1991, 103, 1737-1741; Angew. Chem. Int. Ed. Engl. 1991, 30, 1693-1697.
4. M. Pohl, H. Schmickler, J. Lex, E. Vogel, Angew. Chem. 1991, 103, 1737-1741; Angew. Chem. Int. Ed. Engl. 1991, 30, 1693-1697.
5. E. Vogel, W. Haas, B. Knipp, J. Lex, H. Schmickler, Angew. Chem. 1988, 100, 445-448; Angew. Chem. Inf. Ed. Engl. 1988, 27, 406-409.
6. E. Vogel, W. Haas, B. Knipp, J. Lex, H. Schmickler, Angew. Chem. 1988, 100, 445-448; Angew. Chem. Inf. Ed. Engl. 1988, 27, 406-409.
7. E. Vogel, P. Röhrig, M. Sicken, B. Knipp, A. Herrmann, M. Pohl, H. Schmickler, J. Lex, Angew. Chem. 1989, 101, 1683-1687; Angew. Chem. Int. Ed. Engl. 1989, 28, 1651-1655.
8. E. Vogel, P. Röhrig, M. Sicken, B. Knipp, A. Herrmann, M. Pohl, H. Schmickler, J. Lex, Angew. Chem. 1989, 101, 1683-1687; Angew. Chem. Int. Ed. Engl. 1989, 28, 1651-1655.
9. F. H. Carré, R. J.-P. Corriu, T. Deforth, W. E. Douglas, W. Siebert, W. Weinmann, Angew. Chem. 1998, 110, 654-656; Angew. Chem. Int. Ed. 1998, 37, 652-654.
10. F. H. Carré, R. J.-P. Corriu, T. Deforth, W. E. Douglas, W. Siebert, W. Weinmann, Angew. Chem. 1998, 110, 654-656; Angew. Chem. Int. Ed. 1998, 37, 652-654.
11. [7a] B. König, M. Rödel, P. Bubenitschek, P. G. Jones, Angew. Chem. 1995, 707, 752-754; Angew. Chem. Int. Ed. Engl. 1995, 34, 661-663.
12. [7a] B. König, M. Rödel, P. Bubenitschek, P. G. Jones, Angew. Chem. 1995, 707, 752-754; Angew. Chem. Int. Ed. Engl. 1995, 34, 661-663.
13. [7b] B. König, M. Rödel, P. Bubenitschek, P. G. Jones, I. Thondorf, J. Org. Chem. 1995, 60, 7406-7410.
14. [8a] W. Chen, M. P. Cava, Tetrahedron Lett. 1987, 28, 6025-6026.
15. [8b] T. J. Barton, G. P. Hussmann, J. Org. Chem. 1985, 50, 5881-5882.
16. [8c] M. Gharpure, A. Stoller, F. Bellamy, G. Firnau, V. Snieckus, Synthesis 1991, 1079-1082.
17. S. Martina, V. Enkelmann, G. Wegner, A.-D. Schlüter, Synthesis 1991, 613-615.
18. [10a] B. Wrackmeyer, H. Nöth, Chem. Ber. 1976, 109, 1075-1088.
19. [10b] J. D. Odom, T. F. Moore, R. Goetze, H. Nöth, B. Wrackmeyer, J. Organomet. Chem. 1979, 173, 15-32.
20. 13C-NMR spectra measured at room temperature normally are broadened or even cannot be observed is based on relaxation effects of the boron nucleii. For details see: H. Nöth, B. Wrackmeyer, NMR Spectroscopy of Boron Compounds, Springer Verlag Heidelberg 1978, 6-104.
21. R. A. Jones in The Chemistry of Heterocyclic Compounds Vol. 48, Wiley & Sons New York 1990, 22-42.
22. W. Siebert, Chem. Ber. 1970, 103, 2308-2313.
23. [14a] A. Maderna, H. Pritzkow, W. Siebert, Angew. Chem. 1996, 108, 1664-1666; Angew. Chem. Int. Ed. Engl. 1996, 35, 1501-1503.
24. [14a] A. Maderna, H. Pritzkow, W. Siebert, Angew. Chem. 1996, 108, 1664-1666; Angew. Chem. Int. Ed. Engl. 1996, 35, 1501-1503.
25. [14b] C. Ester, A. Maderna, H. Pritzkow, W. Siebert, Eur. J. Inorg. Chem. to be published. - For reactions with Grignard reagents see: S. Cabiddu, A. Maccioni, M. Secci, Gazz. Chim. Ital. 1972, 102, 555-556.
26. [14b] C. Ester, A. Maderna, H. Pritzkow, W. Siebert, Eur. J. Inorg. Chem. to be published. - For reactions with Grignard reagents see: S. Cabiddu, A. Maccioni, M. Secci, Gazz. Chim. Ital. 1972, 102, 555-556.
27. A. Meller in Gmelin Handbook B 4th Suppl. Vol. 3a, Springer-Verlag Heidelberg 1991, 152-261 and references cited therein.
28. [16a] C. F. Hobbs, C. K. McMillin, E. P. Papapdopoulos, C. A. VanderWerf, J. Am. Chem. Soc. 1962, 84, 43-51.
29. [16b] R. J. Brotherton, A. L. McCloskey, L. L. Petterson, H. Steinberg, J. Am. Chem. Soc. 1960, 82, 6242-6245.
30. [16c] D. W. Aubrey, M. F. Lappert, M. K. Majumdar, J. Chem. Soc. 1962, 4088-4094.
31. [16d] W. Gerrard, H. R. Hudson, E. F. Mooney, J. Chem. Soc. 1960, 5168-5172.
32. [16e] W. Gerrard, M. F. Lappert, B. A. Mountfield, J. Chem. Soc. 1959, 1529-1535.
33. [16f] S. Sorriso, A. Ricci, R. Danieli, J. Organomet. Chem. 1975, 87, 61-65.
34. [17a] G. M. Sheldrick, SHELXS-86, Universität Göttingen 1986.
35. [17b] G. M. Sheldrick, SHELXL-93, Universität Göttingen 1993.