Reactions of allenyltri-n-butylstannane with halides of phosphorus, arsenic, antimony, germanium, tin, and boron. Preparation of propargylic and/or allenic derivatives

Organometallics

Volumn 18, Issue 25, 1999, Pages 5259-5263

  Guillemin, Jean Claude ^a   Malagu, Karine ^a  

^a UNIV RENNES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000946693     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990543l     Document Type: Article

References (37)

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2. Marshall, J. A. Chem. Rev. 1996, 96, 31.
3. (a) Marshall, J. A.; Perkins, J. J. Org. Chem. 1994, 59, 3509.
4. (b) Yamamoto, Y.; Shida, N. Adv. Detailed React. Mech. 1994, 3, 1.
5. (c) Marshall, J. A.; Perkins, J. F.; Wolf, M. A. J. Org. Chem. 1995, 60, 5556.
6. (a) Guillemin, J.-C.; Lassalle, L. Organometallics 1994, 13, 1525.
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9. (d) Lassalle, L.; Legoupy, S.; Guillemin, J.-C. Organometallics 1996, 15, 3466.
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12. (a) Le Serre, S.; Guillemin, J.-C. Organometallics 1997, 16, 5844.
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14. 3. Several allenylhalophosphines or propargylic monohalophosphines have been prepared by other approaches. See for example: Simonnin, M.-P.; Charrier, C. C. R. Acad. Sci. Paris, Ser. C 1968, 267, 550.
15. The presence of small amounts (3%) of allenyldichloroarsine (3b) in arsine 2b cannot be avoided.
16. The allenyldichloroarsine has been prepared previously by the same approach, but without identification of the propargylarsine 2b intermediate. Lassalle, L.; Legoupy, S.; Guillemin, J.-C. Inorg. Chem. 1995, 35, 5694.
17. The presence of small amounts (1-3%) of the propargylic isomer are observed in almost all the allenyl compounds.
18. The preparation of a few pentavalent propargylstibines has been reported: Zhang, L.-J.; Mo, X.-S.; Huang, Y.-Z. J. Organomet. Chem. 1994, 471, 77. To our knowledge, compound 2d is the first trivalent propargylstibine described to date.
19. The preparation of compounds 2e and 3e has been reported: (a) Mironov, V. F.; Gar, T. K. Izv. Akad. Nauk. SSSR, Ser. Khim. 1965, 291. (b) Gar, T. K.; Nosova, V. M.; Kisin, A. V.; Mironov, V. F. Zh. Obshch. Khim. 1978, 48, 838.
20. The preparation of compounds 2e and 3e has been reported: (a) Mironov, V. F.; Gar, T. K. Izv. Akad. Nauk. SSSR, Ser. Khim. 1965, 291. (b) Gar, T. K.; Nosova, V. M.; Kisin, A. V.; Mironov, V. F. Zh. Obshch. Khim. 1978, 48, 838.
21. Vaultier, M.; Carboni, B. Boron. Comprehensive Organometallic Chemistry II; Elsevier: Oxford, New York, Tokyo, 1995; Vol. 11, Chapter 5, pp 191-276.
22. Hall, L. W.; Odom, J. D.; Ellis, P. D. J. Am. Chem. Soc. 1975, 97, 4527.
23. An equilibrium between nonisolated allenyl- and propargylborane has already been proposed, but the latter was considered to be the thermodynamic product: (a) Zweifel, G.; Backlund, S. J.; Leung, T. J. Am. Chem. Soc. 1978, 100, 5561. (b) Zweifel, G.; Pearson, N. R. J. Org. Chem. 1981, 46, 829.
24. An equilibrium between nonisolated allenyl- and propargylborane has already been proposed, but the latter was considered to be the thermodynamic product: (a) Zweifel, G.; Backlund, S. J.; Leung, T. J. Am. Chem. Soc. 1978, 100, 5561. (b) Zweifel, G.; Pearson, N. R. J. Org. Chem. 1981, 46, 829.
25. Le Quan, M.; Cadiot, P. Bull. Soc. Chim. Fr. 1965, 45.
26. Compounds 7 and 8 have been identified by comparison with authentic samples. 7: Gerard, F.; Miginiac, P. J. Organomet. Chem. 1976, 111, 17. 8: Mondon, A. Justus Liebigs Ann. Chem. 1952, 577, 181.
27. Compounds 7 and 8 have been identified by comparison with authentic samples. 7: Gerard, F.; Miginiac, P. J. Organomet. Chem. 1976, 111, 17. 8: Mondon, A. Justus Liebigs Ann. Chem. 1952, 577, 181.
28. For the reaction of 9-allenyl-9-BBN with ketones see: Brown, H. C.; Khire, U. R.; Racheria, U. S. Tetrahedron Lett. 1993, 34, 15.
29. 4 in such reactions has been reported previously. See for example refs 1-3.
30. 3 has been used as a Lewis acid to selectively prepare homoallenic alcohols: (a) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (b) Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1997, 62, 6001.
31. 3 has been used as a Lewis acid to selectively prepare homoallenic alcohols: (a) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (b) Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1997, 62, 6001.
32. Childs, R. F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801.
33. The effectiveness of antimony or bismuth halides as Lewis acids has already been reported previously; see for example: (a) Komatsu, N.; Uda, M.; Suzuki, H.; Takahashi, T.; Domae, T.; Wada, M. Tetrahedron Lett. 1997, 38, 7215. (b) Le Roux, C.; Mandrou, S.; Dubac, J. J. Org. Chem. 1996, 61, 3885.
34. The effectiveness of antimony or bismuth halides as Lewis acids has already been reported previously; see for example: (a) Komatsu, N.; Uda, M.; Suzuki, H.; Takahashi, T.; Domae, T.; Wada, M. Tetrahedron Lett. 1997, 38, 7215. (b) Le Roux, C.; Mandrou, S.; Dubac, J. J. Org. Chem. 1996, 61, 3885.
35. See for example: Masuyama, Y.; Ito, A.; Terada, K.; Kurusu, Y. Chem. Commun. 1998, 2025.
36. Numerous primary α,β-unsaturated compounds have been prepared using this reagent. See ref 4.
37. 4 with propargyl bromide: Shay, R. H.; Diel, B. N.; Schubert, D. M.; Norman, A. D. Inorg. Chem. 1988, 27, 2378.