Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 1. [1,4] O → C and [1,4] C → O Silyl Migrations of Silyl Ethers and Esters Attached to Furan and Thiophene Rings

Journal of Organic Chemistry

Volumn 62, Issue 25, 1997, Pages 8741-8749

  Bures, Edward ^a   Spinazzé, Patrick G ^a   Beese, Giovanna ^a   Hunt, Ian R ^a   Rogers, Christine ^a   Keay, Brian A ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000651888     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971097j     Document Type: Article

References (134)

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39. For use of a benzylic alcohol moiety as an ortho-lithiation director, see: (a) Uemura, M.; Tokuyana, S.; Sakan, T. Chem. Lett. 1975, 1195. (b) Meyer, N.; Seebach, D. Chem. Ber. 1980, 118, 1304. (b) Panetta, C. A.; Dixit, A. S. Synthesis 1981, 59. (d) Uemura, M.; Take, K.; Tobe, K.; Minani, T.; Hayashi, Y. Tetrahedron 1985, 41, 5771. (e) Katsuura, K.; Snieckus, V. Can. J. Chem. 1987, 65, 124. For a synthetic sequence which results in products from the α-lithiation of the benzylic methylene group, see: Katritzky, A. R.; Fan, W.-Q.; Kutagawa, K. Synthesis 1987, 415.
40. For use of a benzylic alcohol moiety as an ortho-lithiation director, see: (a) Uemura, M.; Tokuyana, S.; Sakan, T. Chem. Lett. 1975, 1195. (b) Meyer, N.; Seebach, D. Chem. Ber. 1980, 118, 1304. (b) Panetta, C. A.; Dixit, A. S. Synthesis 1981, 59. (d) Uemura, M.; Take, K.; Tobe, K.; Minani, T.; Hayashi, Y. Tetrahedron 1985, 41, 5771. (e) Katsuura, K.; Snieckus, V. Can. J. Chem. 1987, 65, 124. For a synthetic sequence which results in products from the α-lithiation of the benzylic methylene group, see: Katritzky, A. R.; Fan, W.-Q.; Kutagawa, K. Synthesis 1987, 415.
41. For use of a benzylic alcohol moiety as an ortho-lithiation director, see: (a) Uemura, M.; Tokuyana, S.; Sakan, T. Chem. Lett. 1975, 1195. (b) Meyer, N.; Seebach, D. Chem. Ber. 1980, 118, 1304. (b) Panetta, C. A.; Dixit, A. S. Synthesis 1981, 59. (d) Uemura, M.; Take, K.; Tobe, K.; Minani, T.; Hayashi, Y. Tetrahedron 1985, 41, 5771. (e) Katsuura, K.; Snieckus, V. Can. J. Chem. 1987, 65, 124. For a synthetic sequence which results in products from the α-lithiation of the benzylic methylene group, see: Katritzky, A. R.; Fan, W.-Q.; Kutagawa, K. Synthesis 1987, 415.
42. For use of a benzylic alcohol moiety as an ortho-lithiation director, see: (a) Uemura, M.; Tokuyana, S.; Sakan, T. Chem. Lett. 1975, 1195. (b) Meyer, N.; Seebach, D. Chem. Ber. 1980, 118, 1304. (b) Panetta, C. A.; Dixit, A. S. Synthesis 1981, 59. (d) Uemura, M.; Take, K.; Tobe, K.; Minani, T.; Hayashi, Y. Tetrahedron 1985, 41, 5771. (e) Katsuura, K.; Snieckus, V. Can. J. Chem. 1987, 65, 124. For a synthetic sequence which results in products from the α-lithiation of the benzylic methylene group, see: Katritzky, A. R.; Fan, W.-Q.; Kutagawa, K. Synthesis 1987, 415.
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47. 2) required four silica gel columns (EtOAc:petroleum ether, 1:9) to afford compound 3 in 56% isolated yield.
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49. The spectral data of furan 3, isolated from the reaction involving furan 1 with HMPA, were identical to the major product isolated from reaction of the dianion of compound 10 with tert-butyldimethylsilyl chloride.
50. Oxygen-to-carbon silyl migrations are sometimes referred to as retro[1,n]Brook rearrangements, see: (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G. ; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981. (c) Brook, A. G. Pure Appl. Chem. 1966, 13, 215. (d) Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224, (e) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (f) Brook, A. G.; Bassendale, A. R. Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, pp 149-227. (g) Brook, A. G.; Chrusciel, J. J. Organometallics 1984, 3, 1317 and references therein. For recent references to many [1,n] X → Y silyl migrations, see: He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905.
51. Oxygen-to-carbon silyl migrations are sometimes referred to as retro[1,n]Brook rearrangements, see: (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G. ; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981. (c) Brook, A. G. Pure Appl. Chem. 1966, 13, 215. (d) Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224, (e) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (f) Brook, A. G.; Bassendale, A. R. Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, pp 149-227. (g) Brook, A. G.; Chrusciel, J. J. Organometallics 1984, 3, 1317 and references therein. For recent references to many [1,n] X → Y silyl migrations, see: He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905.
52. Oxygen-to-carbon silyl migrations are sometimes referred to as retro[1,n]Brook rearrangements, see: (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G. ; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981. (c) Brook, A. G. Pure Appl. Chem. 1966, 13, 215. (d) Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224, (e) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (f) Brook, A. G.; Bassendale, A. R. Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, pp 149-227. (g) Brook, A. G.; Chrusciel, J. J. Organometallics 1984, 3, 1317 and references therein. For recent references to many [1,n] X → Y silyl migrations, see: He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905.
53. Oxygen-to-carbon silyl migrations are sometimes referred to as retro[1,n]Brook rearrangements, see: (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G. ; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981. (c) Brook, A. G. Pure Appl. Chem. 1966, 13, 215. (d) Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224, (e) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (f) Brook, A. G.; Bassendale, A. R. Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, pp 149-227. (g) Brook, A. G.; Chrusciel, J. J. Organometallics 1984, 3, 1317 and references therein. For recent references to many [1,n] X → Y silyl migrations, see: He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905.
54. Oxygen-to-carbon silyl migrations are sometimes referred to as retro[1,n]Brook rearrangements, see: (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G. ; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981. (c) Brook, A. G. Pure Appl. Chem. 1966, 13, 215. (d) Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224, (e) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (f) Brook, A. G.; Bassendale, A. R. Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, pp 149-227. (g) Brook, A. G.; Chrusciel, J. J. Organometallics 1984, 3, 1317 and references therein. For recent references to many [1,n] X → Y silyl migrations, see: He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905.
55. Oxygen-to-carbon silyl migrations are sometimes referred to as retro[1,n]Brook rearrangements, see: (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G. ; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981. (c) Brook, A. G. Pure Appl. Chem. 1966, 13, 215. (d) Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224, (e) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (f) Brook, A. G.; Bassendale, A. R. Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, pp 149-227. (g) Brook, A. G.; Chrusciel, J. J. Organometallics 1984, 3, 1317 and references therein. For recent references to many [1,n] X → Y silyl migrations, see: He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905.
56. Oxygen-to-carbon silyl migrations are sometimes referred to as retro[1,n]Brook rearrangements, see: (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G. ; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981. (c) Brook, A. G. Pure Appl. Chem. 1966, 13, 215. (d) Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224, (e) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (f) Brook, A. G.; Bassendale, A. R. Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, pp 149-227. (g) Brook, A. G.; Chrusciel, J. J. Organometallics 1984, 3, 1317 and references therein. For recent references to many [1,n] X → Y silyl migrations, see: He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905.
57. Oxygen-to-carbon silyl migrations are sometimes referred to as retro[1,n]Brook rearrangements, see: (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G. ; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981. (c) Brook, A. G. Pure Appl. Chem. 1966, 13, 215. (d) Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224, (e) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (f) Brook, A. G.; Bassendale, A. R. Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, pp 149-227. (g) Brook, A. G.; Chrusciel, J. J. Organometallics 1984, 3, 1317 and references therein. For recent references to many [1,n] X → Y silyl migrations, see: He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905.
58. (a) Speier, J. L. J. Am. Chem. Soc. 1952, 74,1003.
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63. (f) Rucker, C. Tetrahedron Lett. 1984, 25, 4349. For an example in which the proposed mechanism involves a [1,4] O → C silyl migration, see: Karlsson, J. O.; Nguyen, N. V.; Foland, L. D.; Moore, H. W. J. Am. Chem. Soc. 1985, 107, 3392.
64. (f) Rucker, C. Tetrahedron Lett. 1984, 25, 4349. For an example in which the proposed mechanism involves a [1,4] O → C silyl migration, see: Karlsson, J. O.; Nguyen, N. V.; Foland, L. D.; Moore, H. W. J. Am. Chem. Soc. 1985, 107, 3392.
65. Since 1988, more [1,4] O → C silyl rearrangements have been reported, see: (a) Braun, M. Agnew. Chem., Int. Ed. Engl. 1989, 28, 896. (b) Satoh, T.; Oohara, T; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130. (c) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 43, 6137. (d) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (e) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270. (f) Hoffmann, R. W. Bewersdorf, M. Tetrahedron Lett. 1989, 54, 3130. (g) Hoffmann, R.; Bruckner, R. Chem. Ber. 1992, 125, 1471 and 2731. (h) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Rücker, C. Chem. Rev. 1995, 95, 1009.
66. Since 1988, more [1,4] O → C silyl rearrangements have been reported, see: (a) Braun, M. Agnew. Chem., Int. Ed. Engl. 1989, 28, 896. (b) Satoh, T.; Oohara, T; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130. (c) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 43, 6137. (d) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (e) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270. (f) Hoffmann, R. W. Bewersdorf, M. Tetrahedron Lett. 1989, 54, 3130. (g) Hoffmann, R.; Bruckner, R. Chem. Ber. 1992, 125, 1471 and 2731. (h) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Rücker, C. Chem. Rev. 1995, 95, 1009.
67. Since 1988, more [1,4] O → C silyl rearrangements have been reported, see: (a) Braun, M. Agnew. Chem., Int. Ed. Engl. 1989, 28, 896. (b) Satoh, T.; Oohara, T; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130. (c) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 43, 6137. (d) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (e) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270. (f) Hoffmann, R. W. Bewersdorf, M. Tetrahedron Lett. 1989, 54, 3130. (g) Hoffmann, R.; Bruckner, R. Chem. Ber. 1992, 125, 1471 and 2731. (h) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Rücker, C. Chem. Rev. 1995, 95, 1009.
68. Since 1988, more [1,4] O → C silyl rearrangements have been reported, see: (a) Braun, M. Agnew. Chem., Int. Ed. Engl. 1989, 28, 896. (b) Satoh, T.; Oohara, T; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130. (c) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 43, 6137. (d) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (e) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270. (f) Hoffmann, R. W. Bewersdorf, M. Tetrahedron Lett. 1989, 54, 3130. (g) Hoffmann, R.; Bruckner, R. Chem. Ber. 1992, 125, 1471 and 2731. (h) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Rücker, C. Chem. Rev. 1995, 95, 1009.
69. Since 1988, more [1,4] O → C silyl rearrangements have been reported, see: (a) Braun, M. Agnew. Chem., Int. Ed. Engl. 1989, 28, 896. (b) Satoh, T.; Oohara, T; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130. (c) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 43, 6137. (d) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (e) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270. (f) Hoffmann, R. W. Bewersdorf, M. Tetrahedron Lett. 1989, 54, 3130. (g) Hoffmann, R.; Bruckner, R. Chem. Ber. 1992, 125, 1471 and 2731. (h) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Rücker, C. Chem. Rev. 1995, 95, 1009.
70. Since 1988, more [1,4] O → C silyl rearrangements have been reported, see: (a) Braun, M. Agnew. Chem., Int. Ed. Engl. 1989, 28, 896. (b) Satoh, T.; Oohara, T; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130. (c) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 43, 6137. (d) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (e) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270. (f) Hoffmann, R. W. Bewersdorf, M. Tetrahedron Lett. 1989, 54, 3130. (g) Hoffmann, R.; Bruckner, R. Chem. Ber. 1992, 125, 1471 and 2731. (h) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Rücker, C. Chem. Rev. 1995, 95, 1009.
71. Since 1988, more [1,4] O → C silyl rearrangements have been reported, see: (a) Braun, M. Agnew. Chem., Int. Ed. Engl. 1989, 28, 896. (b) Satoh, T.; Oohara, T; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130. (c) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 43, 6137. (d) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (e) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270. (f) Hoffmann, R. W. Bewersdorf, M. Tetrahedron Lett. 1989, 54, 3130. (g) Hoffmann, R.; Bruckner, R. Chem. Ber. 1992, 125, 1471 and 2731. (h) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Rücker, C. Chem. Rev. 1995, 95, 1009.
72. Since 1988, more [1,4] O → C silyl rearrangements have been reported, see: (a) Braun, M. Agnew. Chem., Int. Ed. Engl. 1989, 28, 896. (b) Satoh, T.; Oohara, T; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130. (c) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 43, 6137. (d) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (e) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270. (f) Hoffmann, R. W. Bewersdorf, M. Tetrahedron Lett. 1989, 54, 3130. (g) Hoffmann, R.; Bruckner, R. Chem. Ber. 1992, 125, 1471 and 2731. (h) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Rücker, C. Chem. Rev. 1995, 95, 1009.
73. Since 1988, more [1,4] O → C silyl rearrangements have been reported, see: (a) Braun, M. Agnew. Chem., Int. Ed. Engl. 1989, 28, 896. (b) Satoh, T.; Oohara, T; Ueda, Y.; Yamakawa, K. J. Org. Chem. 1989, 54, 3130. (c) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 43, 6137. (d) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (e) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270. (f) Hoffmann, R. W. Bewersdorf, M. Tetrahedron Lett. 1989, 54, 3130. (g) Hoffmann, R.; Bruckner, R. Chem. Ber. 1992, 125, 1471 and 2731. (h) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Rücker, C. Chem. Rev. 1995, 95, 1009.
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79. 1H NMR spectrum.
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108. The preparation of compounds 69-73 is discussed in the following paper in this issue; see ref 55.
109. For an example of a reductive desilylation using NaH/HMPA, see: Shekani, M.S.; Kahn, K. M.; Mahmood, K. Tetrahedron Lett. 1988, 29, 6161.
110. Although the silyl migration is finished within a few seconds, we did not go back and repeat all the examples in Table 3. All migrations performed since our initial report with excess NaH in DMF have been finished with a few seconds, so we have no reason to doubt that all the examples in Table 3 would be complete within a few seconds.
111. The reaction time of 56 h in DME for this reaction in our initial communication was an error and all reactions done to date in DME have been complete within 0.5 h.
112. Other [1,4] C → O migrations using sodium ions in diethyl ether have been reported not to proceed. See 34f.
113. KH was not used in DMF since it is known to reduce DMF, see: Brown, C. A. J. Org. Chem. 1974, 39, 3913.
114. (a) Evans, D. A.; Golob, A. M. J. Am. Chem. Soc. 1975, 97, 5765.
115. (b) Magnera, T. F.; Caldwell, G.; Sunner, J.; Ikuta, S.; Kebarle, P. J. Am. Chem. Soc. 1984, 106, 6140.
116. Reichardt, C. Solvent Effects in Organic Chemistry; Verlag Chemie: New York, 1988; pp 232-239.
117. (a) Kolodziejski, W. J. Mol. Struct. 1987, 159, 335.
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120. 3 affinities for some solvents, see: Rauk, A.; Hunt, I. R.; Keay, B. A. J. Org. Chem. 1994, 59, 6808. For theoretical calculations on proton affinities with solvents, see: Yamabe, S.; Hiraa, K.; Wasada, H. J. Chem. Phys. 1992, 96, 10261.
121. 3 affinities for some solvents, see: Rauk, A.; Hunt, I. R.; Keay, B. A. J. Org. Chem. 1994, 59, 6808. For theoretical calculations on proton affinities with solvents, see: Yamabe, S.; Hiraa, K.; Wasada, H. J. Chem. Phys. 1992, 96, 10261.
122. 3 affinities for some solvents, see: Rauk, A.; Hunt, I. R.; Keay, B. A. J. Org. Chem. 1994, 59, 6808. For theoretical calculations on proton affinities with solvents, see: Yamabe, S.; Hiraa, K.; Wasada, H. J. Chem. Phys. 1992, 96, 10261.
123. (a) See ref 43, pp 17-25.
124. (b) Maria, P.-C.; Gal, J.-F. J. Phys. Chem. 1985, 89, 1296 and references therein.
125. Although refs 43-46 indicate that solvent polarity can be related to sodium ion solvation, Abraham and Liszi have reported the ionic solvation free energies for Na and K ions in DMF, THF, and DME. Although the free energy change for Na and K ions was more negative for DMF (-97.3 kcal/mol for Na ions and -79.5 kcal/mol for K ions), when compared to the values for THF and DME (see below), the free energy change for sodium ions in THF (-94.3 kcal/mol) was more negative than that with DME (-92.5 kcal/mol), while with K ions, the values were about the same (-73.3 kcal/mol in THF vs -73.1 kcal/ mol in DME). These results indicate that the observed rate enhancements may be due to a combination of factors, see: Abraham, M. H.; Liszi, J. J. Chem. Soc., Faraday Trans, 1 1978, 1604.
126. Bassindale, A, R.; Taylor, P. G. Reaction Mechanisms of Nucleophilic Attack at Silicon. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1989; Part 1, Chapter 13, pp 839-892.
127. Corriu, R. J. P.; Young, J. C. Hypervalent Silicon Compounds. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1989; Part 2, Chapter 20, pp 1241-1288.
128. (a) Antoniotti, P.; Canepa, C.; Tonachini, G. J. Org. Chem. 1994, 59, 3952.
129. (b) Antoniotti, P.; Tonachini, G. J. Org. Chem. 1993, 58, 3622.
130. 29Si signal was not observed). This does not preclude, however, that a pentavalent intermediate was involved in the migration when excess DMF was added (entry 4, Table 4). The reaction in the presence of DMF was too fast to observe any intermediates by NMR.
131. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
132. Dictionary of Organic Compounds, 2nd Supplement, 5th ed.; Chapman and Hall: London, 1984; pp 215.
133. Aldrich Chemical Catalog. 1994-5, pp 1347.
134. For the preparation of this compound, see the following paper in this issue: Bures, E.; Nieman, J. A.; Yu, S.; Bontront, J.-L. J.; Hunt, I. R.; Rauk, A.; Keay, B.A. J. Org. Chem. 1997, 62, 8750.