On the radical Brook rearrangement. Reactivity of α-silyl alcohols, α- silyl alcohol nitrite esters, and β-haloacylsilanes under radical-forming conditions

Journal of Organic Chemistry

Volumn 65, Issue 8, 2000, Pages 2292-2304

  Paredes, M D ^a   Alonso, R ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; PHOTOLYSIS; STRUCTURE ANALYSIS;

EID: 0034697084     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9912855     Document Type: Article

References (62)

1. For a recent review on the use of silyl groups to control stereochemistry, see: Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. For their use as tethers, see: Stork, G.; Suhi, M. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813-854. Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetrahedron Lett. 1991, 32, 573-576.
2. For a recent review on the use of silyl groups to control stereochemistry, see: Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. For their use as tethers, see: Stork, G.; Suhi, M. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813-854. Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetrahedron Lett. 1991, 32, 573-576.
3. For a recent review on the use of silyl groups to control stereochemistry, see: Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. For their use as tethers, see: Stork, G.; Suhi, M. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813-854. Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetrahedron Lett. 1991, 32, 573-576.
4. For a recent review on the use of silyl groups to control stereochemistry, see: Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. For their use as tethers, see: Stork, G.; Suhi, M. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813-854. Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetrahedron Lett. 1991, 32, 573-576.
5. For a recent review on the use of silyl groups to control stereochemistry, see: Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. For their use as tethers, see: Stork, G.; Suhi, M. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813-854. Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetrahedron Lett. 1991, 32, 573-576.
6. For the radical Brook rearrangement, see refs 3-8. The ionic rearrangement was known previously: Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886-1889. A review can be found in Brook, A. G. Acc. Chem. Rec. 1974, 7, 77-84. For a recent use of the ionic Brook rearrangement as a key step in an efficient [3 + 4] annulation affording seven-membered carbocycles, see: Takeda, K.; Nakajima, A.; Takeda, M.; Hoshii, E. Org. Synth. S. F. Martin, Eds. 1998, 76, 199-213.
7. For the radical Brook rearrangement, see refs 3-8. The ionic rearrangement was known previously: Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886-1889. A review can be found in Brook, A. G. Acc. Chem. Rec. 1974, 7, 77-84. For a recent use of the ionic Brook rearrangement as a key step in an efficient [3 + 4] annulation affording seven-membered carbocycles, see: Takeda, K.; Nakajima, A.; Takeda, M.; Hoshii, E. Org. Synth. S. F. Martin, Eds. 1998, 76, 199-213.
8. For the radical Brook rearrangement, see refs 3-8. The ionic rearrangement was known previously: Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886-1889. A review can be found in Brook, A. G. Acc. Chem. Rec. 1974, 7, 77-84. For a recent use of the ionic Brook rearrangement as a key step in an efficient [3 + 4] annulation affording seven-membered carbocycles, see: Takeda, K.; Nakajima, A.; Takeda, M.; Hoshii, E. Org. Synth. S. F. Martin, Eds. 1998, 76, 199-213.
9. Dalton, J. C.; Bourque, R. A. J. Am. Chem. Soc. 1981, 103, 699-700.
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13. Schiesser, C.; Styles, M. L. J. Chem. Soc., Perkin Trans. 2 1997, 2335-2340.
14. Robertson, J.; Burrows, J. N. Tetrahedron Lett. 1994, 35, 3777-3780.
15. Our preliminary results on the reaction of α-hydroxysilanes 21 with lead tetraacetate have recently been published elsewhere: Paredes, M. D.; Alonso, R. Tetrahedron Lett. 1999, 40, 3973-3976.
16. At present there is no general radical methodology for the preparation of cyclopropane; see for example Srikrishna, A.; Sharma, G. V. R. J. Chem. Soc., Perkin Trans. 1 1997, 177-181. Journet, M.; Malacria, M. J. Org. Chem. 1994, 59, 718-719. Weng, W.; Luh, T. J. Org. Chem. 1993, 58, 5574-5575. Zhang, W.; Dowd, P. Tetrahedron Lett. 1992, 33, 7307-7310 and references therein. See also Curran, D. P.; Gabarda, A. E. Tetrahedron 1999, 55, 3327-3336.
17. At present there is no general radical methodology for the preparation of cyclopropane; see for example Srikrishna, A.; Sharma, G. V. R. J. Chem. Soc., Perkin Trans. 1 1997, 177-181. Journet, M.; Malacria, M. J. Org. Chem. 1994, 59, 718-719. Weng, W.; Luh, T. J. Org. Chem. 1993, 58, 5574-5575. Zhang, W.; Dowd, P. Tetrahedron Lett. 1992, 33, 7307-7310 and references therein. See also Curran, D. P.; Gabarda, A. E. Tetrahedron 1999, 55, 3327-3336.
18. At present there is no general radical methodology for the preparation of cyclopropane; see for example Srikrishna, A.; Sharma, G. V. R. J. Chem. Soc., Perkin Trans. 1 1997, 177-181. Journet, M.; Malacria, M. J. Org. Chem. 1994, 59, 718-719. Weng, W.; Luh, T. J. Org. Chem. 1993, 58, 5574-5575. Zhang, W.; Dowd, P. Tetrahedron Lett. 1992, 33, 7307-7310 and references therein. See also Curran, D. P.; Gabarda, A. E. Tetrahedron 1999, 55, 3327-3336.
19. At present there is no general radical methodology for the preparation of cyclopropane; see for example Srikrishna, A.; Sharma, G. V. R. J. Chem. Soc., Perkin Trans. 1 1997, 177-181. Journet, M.; Malacria, M. J. Org. Chem. 1994, 59, 718-719. Weng, W.; Luh, T. J. Org. Chem. 1993, 58, 5574-5575. Zhang, W.; Dowd, P. Tetrahedron Lett. 1992, 33, 7307-7310 and references therein. See also Curran, D. P.; Gabarda, A. E. Tetrahedron 1999, 55, 3327-3336.
20. At present there is no general radical methodology for the preparation of cyclopropane; see for example Srikrishna, A.; Sharma, G. V. R. J. Chem. Soc., Perkin Trans. 1 1997, 177-181. Journet, M.; Malacria, M. J. Org. Chem. 1994, 59, 718-719. Weng, W.; Luh, T. J. Org. Chem. 1993, 58, 5574-5575. Zhang, W.; Dowd, P. Tetrahedron Lett. 1992, 33, 7307-7310 and references therein. See also Curran, D. P.; Gabarda, A. E. Tetrahedron 1999, 55, 3327-3336.
21. For the preparation of α-silyl alcohols, see Chenede, A.; Abd. Rahman, N.; Fleming, I. Tetrahedron Lett. 1997, 38, 2381-2382 and references therein. (Dimethylphenylsilyl)lithium was prepared from chlorophenyldimethylsilane as described by: Fleming, I.; Newton, T. W.; Roessler, F. J. Chem. Soc., Perkin Trans, 1 1981, 2527-2532.
22. For the preparation of α-silyl alcohols, see Chenede, A.; Abd. Rahman, N.; Fleming, I. Tetrahedron Lett. 1997, 38, 2381-2382 and references therein. (Dimethylphenylsilyl)lithium was prepared from chlorophenyldimethylsilane as described by: Fleming, I.; Newton, T. W.; Roessler, F. J. Chem. Soc., Perkin Trans, 1 1981, 2527-2532.
23. Barrett, A. G. M.; Hill, J. Tetrahedron Lett. 1991, 32, 3285-3288.
24. This substrate had been prepared before: Fleming, I.; Ghosh, U. J. Chem. Soc., Perkin Trans. 1 1994, 257-262.
25. Typical examples of the addition of the dimethylphenylsilyllithium to ketones are described in Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 831-834; Bishop, P. M.; Pearson, J. R.; Sutherland, J. K. J. Chem. Soc., Chem. Commun. 1983, 123-124. Vedejs, E.; Arnost, M. J.; Eustache, J. M.; Krafft, G. A. J. Org. Chem. 1982, 47, 4384-4386.
26. Typical examples of the addition of the dimethylphenylsilyllithium to ketones are described in Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 831-834; Bishop, P. M.; Pearson, J. R.; Sutherland, J. K. J. Chem. Soc., Chem. Commun. 1983, 123-124. Vedejs, E.; Arnost, M. J.; Eustache, J. M.; Krafft, G. A. J. Org. Chem. 1982, 47, 4384-4386.
27. Typical examples of the addition of the dimethylphenylsilyllithium to ketones are described in Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 831-834; Bishop, P. M.; Pearson, J. R.; Sutherland, J. K. J. Chem. Soc., Chem. Commun. 1983, 123-124. Vedejs, E.; Arnost, M. J.; Eustache, J. M.; Krafft, G. A. J. Org. Chem. 1982, 47, 4384-4386.
28. Mancuso, A. J.; Huang, S. L.; Swern, D. J. J. Org. Chem. 1978, 43, 2480-2482.
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31. (a) Evidence for the formation of alkoxyl radicals from alcohols on treatment with LTA has been obtained from ESR studies and from the isolation of epimeric products derived from reversible fragmentation of these intermediates; a detailed and well-documented mechanistic description of this reaction is given by Mihailovic M. Lj.; Cekovic, Z.; Lorenc, Lj. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., de Jonge, C. R. H. I., Eds.; Plenum Press: New York 1986; Chapter 14, pp 741-816.
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33. This is the first reported method for direct conversion of α-silyl alcohols to acetals. It complements the known oxidations of these substrates to aldehydes: (a) Fleming, I.; Ghosh, U. J. Chem. Soc., Perkin Trans. 1 1994, 257-262, and to acylsilanes:
34. (b) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198-2200.
35. A search of Chemical Abstracts for acyl-silyl acetal substructures found just 23 references between 1967 and mid 1997.
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46. A silyl group can stabilize β-carbon radicals through "σ-πn hyperconjugation" and " p-d homoconjugation". See Hwu, J. R.; King, K. Y.; Wu, I.-F.; Hakimelahi, G. H. Tetrahedron Lett. 1998, 39, 3721-3724. Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819-824. Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644-646. N. Auner, R. Walsh, J. Westrup. J. Chem. Soc., Chem. Commun. 1986, 207-208; Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208-211. Kawamura, T. J.; Kochi. K. J. Am. Chem. Soc. 1972, 94, 648-650.
47. A silyl group can stabilize β-carbon radicals through "σ-πn hyperconjugation" and " p-d homoconjugation". See Hwu, J. R.; King, K. Y.; Wu, I.-F.; Hakimelahi, G. H. Tetrahedron Lett. 1998, 39, 3721-3724. Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819-824. Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644-646. N. Auner, R. Walsh, J. Westrup. J. Chem. Soc., Chem. Commun. 1986, 207-208; Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208-211. Kawamura, T. J.; Kochi. K. J. Am. Chem. Soc. 1972, 94, 648-650.
48. A silyl group can stabilize β-carbon radicals through "σ-πn hyperconjugation" and " p-d homoconjugation". See Hwu, J. R.; King, K. Y.; Wu, I.-F.; Hakimelahi, G. H. Tetrahedron Lett. 1998, 39, 3721-3724. Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819-824. Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644-646. N. Auner, R. Walsh, J. Westrup. J. Chem. Soc., Chem. Commun. 1986, 207-208; Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208-211. Kawamura, T. J.; Kochi. K. J. Am. Chem. Soc. 1972, 94, 648-650.
49. A silyl group can stabilize β-carbon radicals through "σ-πn hyperconjugation" and " p-d homoconjugation". See Hwu, J. R.; King, K. Y.; Wu, I.-F.; Hakimelahi, G. H. Tetrahedron Lett. 1998, 39, 3721-3724. Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819-824. Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644-646. N. Auner, R. Walsh, J. Westrup. J. Chem. Soc., Chem. Commun. 1986, 207-208; Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208-211. Kawamura, T. J.; Kochi. K. J. Am. Chem. Soc. 1972, 94, 648-650.
50. A silyl group can stabilize β-carbon radicals through "σ-πn hyperconjugation" and " p-d homoconjugation". See Hwu, J. R.; King, K. Y.; Wu, I.-F.; Hakimelahi, G. H. Tetrahedron Lett. 1998, 39, 3721-3724. Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819-824. Davidson, I. M. T.; Barton, T. J.; Hughes, K. J.; Ijadi-Maghsoodi, S.; Revis, A.; Paul, G. C. Organometallics 1987, 6, 644-646. N. Auner, R. Walsh, J. Westrup. J. Chem. Soc., Chem. Commun. 1986, 207-208; Jackson, R. A.; Ingold, K. U.; Griller, D.; Nazran, A. S. J. Am. Chem. Soc. 1985, 107, 208-211. Kawamura, T. J.; Kochi. K. J. Am. Chem. Soc. 1972, 94, 648-650.
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61. As indicated, nitrites 25i and 25j were obtained as mixtures with their alcohol precursors, 21i and 21j, respectively. These mixtures were used in the photolysis experiments.
62. In line with our result on the acylsilane 56, Curran observed a similar rearrangement of an α-seleno cyclopropyloxy radical obtained by 1,3-exo cyclization of a β-acylgermane carbon radical analogous to 26a: opening was faster than the alternative β-elimination of selenyl radicals to the corresponding cyclopropanone: Curran, D. P.; Diederichsen, U.; Palovich, M. J. Am. Chem. Soc. 1997, 119, 4797-4804.