A facile synthesis of α-phenylchalcogeno(S, Se) α,β-unsaturated esters from ethyl α-bromo-α-phenylchalcogeno acetates

Synthetic Communications

Volumn 28, Issue 18, 1998, Pages 3371-3380

  Silveira, Claudio C ^a   Botega, Clausia S ^a   Rhoden, Cristiano R B ^a   Nunes, Marta R S ^a   Braga, Antonio L ^a   Lenardão, Eder J ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b FEDERAL UNIVERSITY OF PELOTAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE; ESTER; SELENIUM;

ARTICLE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0031753170     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004444     Document Type: Article

References (49)

1. a) Petragnani, N. Best Synthetic Methods-Tellurium in Organic Synthesis, Academic Press, London, 1994;
2. b) Petragnani, N. and Comasseto, J. V. Synthesis 1991, 793 and 897;
3. c) Petragnani, N. and Comasseto, J. V. Synthesis, 1986, 1;
4. d) Engman, L. Acc. Chem. Res., 1985, 18, 274.
5. Zhou, Z. L.; Huang, Y. Z.; Shi, L. L. and Hu, J. J. Org. Chem. 1992, 57, 6598 and references 3 and 4 therein; Osuka, A. and Suzuki, H. Tetrahedron Lett. 1983, 24, 5109; Zhou, Z. L., Huang, Y. Z. and Shi, L. L. J. Chem. Soc., Chem. Commun., 1992, 986; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron Lett., 1992, 5827.
6. Zhou, Z. L.; Huang, Y. Z.; Shi, L. L. and Hu, J. J. Org. Chem. 1992, 57, 6598 and references 3 and 4 therein; Osuka, A. and Suzuki, H. Tetrahedron Lett. 1983, 24, 5109; Zhou, Z. L., Huang, Y. Z. and Shi, L. L. J. Chem. Soc., Chem. Commun., 1992, 986; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron Lett., 1992, 5827.
7. Zhou, Z. L.; Huang, Y. Z.; Shi, L. L. and Hu, J. J. Org. Chem. 1992, 57, 6598 and references 3 and 4 therein; Osuka, A. and Suzuki, H. Tetrahedron Lett. 1983, 24, 5109; Zhou, Z. L., Huang, Y. Z. and Shi, L. L. J. Chem. Soc., Chem. Commun., 1992, 986; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron Lett., 1992, 5827.
8. Zhou, Z. L.; Huang, Y. Z.; Shi, L. L. and Hu, J. J. Org. Chem. 1992, 57, 6598 and references 3 and 4 therein; Osuka, A. and Suzuki, H. Tetrahedron Lett. 1983, 24, 5109; Zhou, Z. L., Huang, Y. Z. and Shi, L. L. J. Chem. Soc., Chem. Commun., 1992, 986; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron Lett., 1992, 5827.
9. Tang, Y.; Huang, Y. Z.; Dai, L. X.; Sun, J., Xia, W. J. Org. Chem. 1997, 62, 954; Tang, Y.; Huang, Y. Z.; Dai, L. X.; Chi, Z. F. and Shi, L. P. J. Org. Chem. 1996, 61, 5762; Tang, Y.; Chi, Z. F.; Huang, Y. Z.; Dai, L. X. and Yu, Y. H. Tetrahedron, 1996, 52, 8747; Huang, Y. Z.; Tang, Y.; Zhou, Z. L.; Xia, W. and Shi, L. P. J. Chem. Soc., Perkin Trans. 1, 1994, 893 and references 6 and 7 therein; Zhong, Q.; Shao, J. and Liu, C. Synth. Commun., 1992, 22, 489; Tamagaki, S.; Akatsuka, R. and Kozuka, S. Bull. Chem. Soc. Jpn., 1980, 53, 817.
10. Tang, Y.; Huang, Y. Z.; Dai, L. X.; Sun, J., Xia, W. J. Org. Chem. 1997, 62, 954; Tang, Y.; Huang, Y. Z.; Dai, L. X.; Chi, Z. F. and Shi, L. P. J. Org. Chem. 1996, 61, 5762; Tang, Y.; Chi, Z. F.; Huang, Y. Z.; Dai, L. X. and Yu, Y. H. Tetrahedron, 1996, 52, 8747; Huang, Y. Z.; Tang, Y.; Zhou, Z. L.; Xia, W. and Shi, L. P. J. Chem. Soc., Perkin Trans. 1, 1994, 893 and references 6 and 7 therein; Zhong, Q.; Shao, J. and Liu, C. Synth. Commun., 1992, 22, 489; Tamagaki, S.; Akatsuka, R. and Kozuka, S. Bull. Chem. Soc. Jpn., 1980, 53, 817.
11. Tang, Y.; Huang, Y. Z.; Dai, L. X.; Sun, J., Xia, W. J. Org. Chem. 1997, 62, 954; Tang, Y.; Huang, Y. Z.; Dai, L. X.; Chi, Z. F. and Shi, L. P. J. Org. Chem. 1996, 61, 5762; Tang, Y.; Chi, Z. F.; Huang, Y. Z.; Dai, L. X. and Yu, Y. H. Tetrahedron, 1996, 52, 8747; Huang, Y. Z.; Tang, Y.; Zhou, Z. L.; Xia, W. and Shi, L. P. J. Chem. Soc., Perkin Trans. 1, 1994, 893 and references 6 and 7 therein; Zhong, Q.; Shao, J. and Liu, C. Synth. Commun., 1992, 22, 489; Tamagaki, S.; Akatsuka, R. and Kozuka, S. Bull. Chem. Soc. Jpn., 1980, 53, 817.
12. Tang, Y.; Huang, Y. Z.; Dai, L. X.; Sun, J., Xia, W. J. Org. Chem. 1997, 62, 954; Tang, Y.; Huang, Y. Z.; Dai, L. X.; Chi, Z. F. and Shi, L. P. J. Org. Chem. 1996, 61, 5762; Tang, Y.; Chi, Z. F.; Huang, Y. Z.; Dai, L. X. and Yu, Y. H. Tetrahedron, 1996, 52, 8747; Huang, Y. Z.; Tang, Y.; Zhou, Z. L.; Xia, W. and Shi, L. P. J. Chem. Soc., Perkin Trans. 1, 1994, 893 and references 6 and 7 therein; Zhong, Q.; Shao, J. and Liu, C. Synth. Commun., 1992, 22, 489; Tamagaki, S.; Akatsuka, R. and Kozuka, S. Bull. Chem. Soc. Jpn., 1980, 53, 817.
13. Tang, Y.; Huang, Y. Z.; Dai, L. X.; Sun, J., Xia, W. J. Org. Chem. 1997, 62, 954; Tang, Y.; Huang, Y. Z.; Dai, L. X.; Chi, Z. F. and Shi, L. P. J. Org. Chem. 1996, 61, 5762; Tang, Y.; Chi, Z. F.; Huang, Y. Z.; Dai, L. X. and Yu, Y. H. Tetrahedron, 1996, 52, 8747; Huang, Y. Z.; Tang, Y.; Zhou, Z. L.; Xia, W. and Shi, L. P. J. Chem. Soc., Perkin Trans. 1, 1994, 893 and references 6 and 7 therein; Zhong, Q.; Shao, J. and Liu, C. Synth. Commun., 1992, 22, 489; Tamagaki, S.; Akatsuka, R. and Kozuka, S. Bull. Chem. Soc. Jpn., 1980, 53, 817.
14. Tang, Y.; Huang, Y. Z.; Dai, L. X.; Sun, J., Xia, W. J. Org. Chem. 1997, 62, 954; Tang, Y.; Huang, Y. Z.; Dai, L. X.; Chi, Z. F. and Shi, L. P. J. Org. Chem. 1996, 61, 5762; Tang, Y.; Chi, Z. F.; Huang, Y. Z.; Dai, L. X. and Yu, Y. H. Tetrahedron, 1996, 52, 8747; Huang, Y. Z.; Tang, Y.; Zhou, Z. L.; Xia, W. and Shi, L. P. J. Chem. Soc., Perkin Trans. 1, 1994, 893 and references 6 and 7 therein; Zhong, Q.; Shao, J. and Liu, C. Synth. Commun., 1992, 22, 489; Tamagaki, S.; Akatsuka, R. and Kozuka, S. Bull. Chem. Soc. Jpn., 1980, 53, 817.
15. Li, S. W.; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. J. Chem. Soc., Perkin Trans. 1, 1991, 1099; Zhou, Z. L.; Shi, L. L. and Huang, Y. Z. J. Chem. Soc., Perkin Trans. 1, 1991, 1931; Shi, L. L.; Zhou, Z. L. and Huang, Y. Z. J. Chem. Soc., Perkin Trans. 1, 1990, 2847.
16. Li, S. W.; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. J. Chem. Soc., Perkin Trans. 1, 1991, 1099; Zhou, Z. L.; Shi, L. L. and Huang, Y. Z. J. Chem. Soc., Perkin Trans. 1, 1991, 1931; Shi, L. L.; Zhou, Z. L. and Huang, Y. Z. J. Chem. Soc., Perkin Trans. 1, 1990, 2847.
17. Li, S. W.; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. J. Chem. Soc., Perkin Trans. 1, 1991, 1099; Zhou, Z. L.; Shi, L. L. and Huang, Y. Z. J. Chem. Soc., Perkin Trans. 1, 1991, 1931; Shi, L. L.; Zhou, Z. L. and Huang, Y. Z. J. Chem. Soc., Perkin Trans. 1, 1990, 2847.
18. Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 49, 6821 and reference 4 therein; Huang, Y. Z.; Shi, L. L.; Li, S. W.; Wen, X. Q. J. Chem. Soc., Perkin Trans. 1, 1989, 2397; Matsuki, T.; Xing Hu, N.; Aso, Y.; Otsubo T. and Ogura, F. Bull. Chem. Soc. Jpn., 1989, 62, 2105; Huang, X.; Xie, L. and Wu, H. Tetrahedron Lett., 1987, 28, 801; Shao, J. G.; Zhong, Q.; Liao, H. P.; Liu, C. Q. and Zhou, J. F. Org. Prep. Proced. Int., 1992, 24, 520; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 31, 6821; Li, S. W.; Huang, Y. Z. and Shi, L. L. Chem. Ber., 1990, 1441.
19. Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 49, 6821 and reference 4 therein; Huang, Y. Z.; Shi, L. L.; Li, S. W.; Wen, X. Q. J. Chem. Soc., Perkin Trans. 1, 1989, 2397; Matsuki, T.; Xing Hu, N.; Aso, Y.; Otsubo T. and Ogura, F. Bull. Chem. Soc. Jpn., 1989, 62, 2105; Huang, X.; Xie, L. and Wu, H. Tetrahedron Lett., 1987, 28, 801; Shao, J. G.; Zhong, Q.; Liao, H. P.; Liu, C. Q. and Zhou, J. F. Org. Prep. Proced. Int., 1992, 24, 520; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 31, 6821; Li, S. W.; Huang, Y. Z. and Shi, L. L. Chem. Ber., 1990, 1441.
20. Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 49, 6821 and reference 4 therein; Huang, Y. Z.; Shi, L. L.; Li, S. W.; Wen, X. Q. J. Chem. Soc., Perkin Trans. 1, 1989, 2397; Matsuki, T.; Xing Hu, N.; Aso, Y.; Otsubo T. and Ogura, F. Bull. Chem. Soc. Jpn., 1989, 62, 2105; Huang, X.; Xie, L. and Wu, H. Tetrahedron Lett., 1987, 28, 801; Shao, J. G.; Zhong, Q.; Liao, H. P.; Liu, C. Q. and Zhou, J. F. Org. Prep. Proced. Int., 1992, 24, 520; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 31, 6821; Li, S. W.; Huang, Y. Z. and Shi, L. L. Chem. Ber., 1990, 1441.
21. Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 49, 6821 and reference 4 therein; Huang, Y. Z.; Shi, L. L.; Li, S. W.; Wen, X. Q. J. Chem. Soc., Perkin Trans. 1, 1989, 2397; Matsuki, T.; Xing Hu, N.; Aso, Y.; Otsubo T. and Ogura, F. Bull. Chem. Soc. Jpn., 1989, 62, 2105; Huang, X.; Xie, L. and Wu, H. Tetrahedron Lett., 1987, 28, 801; Shao, J. G.; Zhong, Q.; Liao, H. P.; Liu, C. Q. and Zhou, J. F. Org. Prep. Proced. Int., 1992, 24, 520; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 31, 6821; Li, S. W.; Huang, Y. Z. and Shi, L. L. Chem. Ber., 1990, 1441.
22. Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 49, 6821 and reference 4 therein; Huang, Y. Z.; Shi, L. L.; Li, S. W.; Wen, X. Q. J. Chem. Soc., Perkin Trans. 1, 1989, 2397; Matsuki, T.; Xing Hu, N.; Aso, Y.; Otsubo T. and Ogura, F. Bull. Chem. Soc. Jpn., 1989, 62, 2105; Huang, X.; Xie, L. and Wu, H. Tetrahedron Lett., 1987, 28, 801; Shao, J. G.; Zhong, Q.; Liao, H. P.; Liu, C. Q. and Zhou, J. F. Org. Prep. Proced. Int., 1992, 24, 520; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 31, 6821; Li, S. W.; Huang, Y. Z. and Shi, L. L. Chem. Ber., 1990, 1441.
23. Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 49, 6821 and reference 4 therein; Huang, Y. Z.; Shi, L. L.; Li, S. W.; Wen, X. Q. J. Chem. Soc., Perkin Trans. 1, 1989, 2397; Matsuki, T.; Xing Hu, N.; Aso, Y.; Otsubo T. and Ogura, F. Bull. Chem. Soc. Jpn., 1989, 62, 2105; Huang, X.; Xie, L. and Wu, H. Tetrahedron Lett., 1987, 28, 801; Shao, J. G.; Zhong, Q.; Liao, H. P.; Liu, C. Q. and Zhou, J. F. Org. Prep. Proced. Int., 1992, 24, 520; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 31, 6821; Li, S. W.; Huang, Y. Z. and Shi, L. L. Chem. Ber., 1990, 1441.
24. Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 49, 6821 and reference 4 therein; Huang, Y. Z.; Shi, L. L.; Li, S. W.; Wen, X. Q. J. Chem. Soc., Perkin Trans. 1, 1989, 2397; Matsuki, T.; Xing Hu, N.; Aso, Y.; Otsubo T. and Ogura, F. Bull. Chem. Soc. Jpn., 1989, 62, 2105; Huang, X.; Xie, L. and Wu, H. Tetrahedron Lett., 1987, 28, 801; Shao, J. G.; Zhong, Q.; Liao, H. P.; Liu, C. Q. and Zhou, J. F. Org. Prep. Proced. Int., 1992, 24, 520; Zhou, Z. L.; Huang, Y. Z. and Shi, L. L. Tetrahedron, 1993, 31, 6821; Li, S. W.; Huang, Y. Z. and Shi, L. L. Chem. Ber., 1990, 1441.
25. Dabdoub, M. J.; Guerrero Jr., P. G. and Silveira, C. C. J. Organomet. Chem., 1993, 460, 31.
26. a) Silveira, C. C.; Braga, A. L.; Machado, A.; Fiorin, G. L. and Dabdoub, M. J. Tetrahedron Lett., 1996, 37, 9173;
27. b) Silveira, C. C.; Araujo, M. A.; Lenardão, E. J.; Braga, A. L. and Dabdoub, M. J. Synthesis, 1995, 1305;
28. c) Silveira, C. C., Lenardão, E. J.; Dabdoub, M. J. and Comassseto, J. V. Tetrahedron Lett., 1991, 32, 5741.
29. Silveira, C. C.; Begnini, M. L.; Boeck, P.; Braga, A.L. Synthesis 1997, 221; Braga, A.L.; Zeni, G.; Andrade, L. H.; Silveira, C. C. Synlett 1997, 595; Silveira, C. C.; Perin, G. and Braga, A. L. Tetrahedron Lett., 1995, 36, 7361; Silveira, C. C.; Perin, G.; Braga, A. L. and Petragnani, N. Synlett, 1995, 58; Silveira, C. C.; Perin, G. and Braga, A. L. J. Chem. Res.(S), 1994, 492; Braga, A. L.; Reckziegel, A.; Silveira, C. C. and Comasseto, J. V. Synth. Commun., 1994, 24, 1165.
30. Silveira, C. C.; Begnini, M. L.; Boeck, P.; Braga, A.L. Synthesis 1997, 221; Braga, A.L.; Zeni, G.; Andrade, L. H.; Silveira, C. C. Synlett 1997, 595; Silveira, C. C.; Perin, G. and Braga, A. L. Tetrahedron Lett., 1995, 36, 7361; Silveira, C. C.; Perin, G.; Braga, A. L. and Petragnani, N. Synlett, 1995, 58; Silveira, C. C.; Perin, G. and Braga, A. L. J. Chem. Res.(S), 1994, 492; Braga, A. L.; Reckziegel, A.; Silveira, C. C. and Comasseto, J. V. Synth. Commun., 1994, 24, 1165.
31. Silveira, C. C.; Begnini, M. L.; Boeck, P.; Braga, A.L. Synthesis 1997, 221; Braga, A.L.; Zeni, G.; Andrade, L. H.; Silveira, C. C. Synlett 1997, 595; Silveira, C. C.; Perin, G. and Braga, A. L. Tetrahedron Lett., 1995, 36, 7361; Silveira, C. C.; Perin, G.; Braga, A. L. and Petragnani, N. Synlett, 1995, 58; Silveira, C. C.; Perin, G. and Braga, A. L. J. Chem. Res.(S), 1994, 492; Braga, A. L.; Reckziegel, A.; Silveira, C. C. and Comasseto, J. V. Synth. Commun., 1994, 24, 1165.
32. Silveira, C. C.; Begnini, M. L.; Boeck, P.; Braga, A.L. Synthesis 1997, 221; Braga, A.L.; Zeni, G.; Andrade, L. H.; Silveira, C. C. Synlett 1997, 595; Silveira, C. C.; Perin, G. and Braga, A. L. Tetrahedron Lett., 1995, 36, 7361; Silveira, C. C.; Perin, G.; Braga, A. L. and Petragnani, N. Synlett, 1995, 58; Silveira, C. C.; Perin, G. and Braga, A. L. J. Chem. Res.(S), 1994, 492; Braga, A. L.; Reckziegel, A.; Silveira, C. C. and Comasseto, J. V. Synth. Commun., 1994, 24, 1165.
33. Silveira, C. C.; Begnini, M. L.; Boeck, P.; Braga, A.L. Synthesis 1997, 221; Braga, A.L.; Zeni, G.; Andrade, L. H.; Silveira, C. C. Synlett 1997, 595; Silveira, C. C.; Perin, G. and Braga, A. L. Tetrahedron Lett., 1995, 36, 7361; Silveira, C. C.; Perin, G.; Braga, A. L. and Petragnani, N. Synlett, 1995, 58; Silveira, C. C.; Perin, G. and Braga, A. L. J. Chem. Res.(S), 1994, 492; Braga, A. L.; Reckziegel, A.; Silveira, C. C. and Comasseto, J. V. Synth. Commun., 1994, 24, 1165.
34. Silveira, C. C.; Begnini, M. L.; Boeck, P.; Braga, A.L. Synthesis 1997, 221; Braga, A.L.; Zeni, G.; Andrade, L. H.; Silveira, C. C. Synlett 1997, 595; Silveira, C. C.; Perin, G. and Braga, A. L. Tetrahedron Lett., 1995, 36, 7361; Silveira, C. C.; Perin, G.; Braga, A. L. and Petragnani, N. Synlett, 1995, 58; Silveira, C. C.; Perin, G. and Braga, A. L. J. Chem. Res.(S), 1994, 492; Braga, A. L.; Reckziegel, A.; Silveira, C. C. and Comasseto, J. V. Synth. Commun., 1994, 24, 1165.
35. Huang, Z. Z.; Huang, X. and Huang, Y. Z. Tetrahedron Lett., 1995, 36, 425; Huang, Z. Z.; Huang, X. and Huang, Y. Z. J. Chem. Res. (S), 1995, 206; Huang, Z. Z.; Huang, X. and Huang, Y. Z. J. Organomet. Chem.,1995, 490, C23.
36. Huang, Z. Z.; Huang, X. and Huang, Y. Z. Tetrahedron Lett., 1995, 36, 425; Huang, Z. Z.; Huang, X. and Huang, Y. Z. J. Chem. Res. (S), 1995, 206; Huang, Z. Z.; Huang, X. and Huang, Y. Z. J. Organomet. Chem.,1995, 490, C23.
37. Huang, Z. Z.; Huang, X. and Huang, Y. Z. Tetrahedron Lett., 1995, 36, 425; Huang, Z. Z.; Huang, X. and Huang, Y. Z. J. Chem. Res. (S), 1995, 206; Huang, Z. Z.; Huang, X. and Huang, Y. Z. J. Organomet. Chem.,1995, 490, C23.
38. a) Robinson, C. N. and Shaffer, A. A. J. Org. Chem, 1993, 58, 3563;
39. b) Wadsworth, D. H. and Detty, M. R. J. Org. Chem., 1980, 45, 4611;
40. c) Quendo, A.; Ali, S. M. and Rousseau, G. J. Org. Chem., 1992, 57, 6890.
41. For the preparation of 3 from α,β-unsaturated esters see: d) Janousek, Z.; Piettre, S.; Gorissen-Hervens, F. and Viehe, H. G. J. Organomet. Chem., 1983, 250, 197; e) Hase, T. A. and Kukkola, P. Synth. Commun., 1980, 10, 451; f) Piettre, S.; Janouzek, Z.; Merenyl, R. and Viehe, H. G. Tetrahedron, 1985, 41, 2527.
42. For the preparation of 3 from α,β-unsaturated esters see: d) Janousek, Z.; Piettre, S.; Gorissen-Hervens, F. and Viehe, H. G. J. Organomet. Chem., 1983, 250, 197; e) Hase, T. A. and Kukkola, P. Synth. Commun., 1980, 10, 451; f) Piettre, S.; Janouzek, Z.; Merenyl, R. and Viehe, H. G. Tetrahedron, 1985, 41, 2527.
43. For the preparation of 3 from α,β-unsaturated esters see: d) Janousek, Z.; Piettre, S.; Gorissen-Hervens, F. and Viehe, H. G. J. Organomet. Chem., 1983, 250, 197; e) Hase, T. A. and Kukkola, P. Synth. Commun., 1980, 10, 451; f) Piettre, S.; Janouzek, Z.; Merenyl, R. and Viehe, H. G. Tetrahedron, 1985, 41, 2527.
44. Böhme, H. and Krack, W. Liebigs Ann. Chem., 1977, 51.
45. a) Brownbridge, P.; Durman, J.; Hunt, P. G. and Warren, S. J. Chem. Soc., Perkin Trans. 1, 1986, 1947;
46. b) Durman, J.; Ian Grayson, J.; Hunt, P. G. and Warren, S. J. Chem. Soc., Perkin Trans. 1, 1986, 1939 and references therein.
47. Yamagiwa, S.; Hoshi, N.; Sato, H.; Kosugi, H. and Uda, H. J. Chem. Soc., Perkin Trans. 1, 1978, 214;
48. Engman, L. and Cava, M. P. Synth. Commun., 1982, 12, 163.
49. Perrin, D. D. and Armarego, W. L. F. Purification of Laboratory Chemicals, Pergamon Press, New York, 3rd. edition, 1988.