Functionalization of thiocrown ethers containing the thioacetal unit

Tetrahedron Letters

Volumn 39, Issue 35, 1998, Pages 6357-6360

  Buter, Jan ^a   Meijer, Renzo H ^a   Kellogg, Richard M ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; MACROCYCLIC COMPOUND; SULFIDE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032572889     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01308-2     Document Type: Article

References (20)

1. 1. See, for example: S.R. Cooper in "Crown Compounds. Towards Future Applications", VCH Publishers, Inc., New York, 1992, pp. 285-302.
2. 2. a) J. Buter, R.M. Kellogg, J. Chem. Soc., Chem. Commun., 1980, 460;
3. b) J. Buter, R.M. Kellogg, J. Org. Chem., 1987, 46, 4481;
4. c) J. Buter, R.M. Keliogg, Org. Synth., 1987, 65, 150.
5. 3. a) J. Buter, R.M. Kellogg, F. van Bolhuis, J. Chem. Soc., Chem. Commun., 1990, 282;
6. b) J. Buter, R.M. Kellogg, F. van Bolhuis, J. Chem. Soc., Chem. Commun., 1991, 910;
7. c) H. Xianming, R.M. Kellogg, F. van Bolhuis, J. Chem. Soc. Perkin Trans. I, 1994, 707;
8. d) J.J.H. Edema, M. Hoogenraad, R.M. Kellogg, A. Meetsma, A.L. Spek, J. Org. Chem., 1993, 58, 5383;
9. e) B. de Groot, S.J. Loeb, Inorg. Chem., 1989, 28, 3573.
10. 4. M. Kolb, Synthesis, 1990, 171 and references therein
11. 5. D. Seebach, Synthesis, 1969, 17 and references therein
12. 6. a) C.G. Kruse, N.L.J.M. Broekhof, A. Wijsman, A. van der Gen, Tetrahedron Lett., 1977, 885; C.G. Kruse, A. Wijsman, A. van der Gen, J. Org. Chem., 1979, 44, 1847.
13. 6. a) C.G. Kruse, N.L.J.M. Broekhof, A. Wijsman, A. van der Gen, Tetrahedron Lett., 1977, 885; C.G. Kruse, A. Wijsman, A. van der Gen, J. Org. Chem., 1979, 44, 1847.
14. 7. F.A. Carey, A.S. Court, J. Org. Chem., 1972, 37, 1926.
15. 8. D. Seebach, E.J. Corey, J. Org. Chem., 1975, 40, 231.
16. -) calcd. 268.045, obsd. 268.045.
17. 8 The problem can be avoided by carrying out the reactions at -100°C; the silyl derivative (shown) is readily obtained and condensations with, for example, 2-thiophene aldehyde proceed cleanly under these conditions. (equation presented)
18. 3SiCl were added. The silyl derivatives were isolated and purified by vacuum distillation. The silytated derivatives were again deprotonated with n-BuLi at -60°C and then one equivalent of aldehyde was added. The olefinic products were obtained on work-up. In some cases heavy oils were formed that were difficult to purify.
19. 12. V. P. Rao, Y.M. Cai, A. K.-Y. Jeu, J. Chem. Soc. Chem. Commun., 1994, 1689.
20. 13. A. K.-Y. Jeu, V. P. Rao, K.J. Drost, K. Y. Wong, M.P. Cava, J. Chem. Soc. Chem. Commun., 1994, 2057.