Synthesis and Conversions of Substituted o-[(Trimethylsilyl)methyl]benzyl p-Tolyl Sulfones to o-Quinodimethanes and Products Thereof

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2072-2085

  Lenihan, Brian D ^a   Shechter, Harold ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000067622     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970592c     Document Type: Article

References (66)

1. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
2. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
3. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
4. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
5. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
6. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
7. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
8. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
9. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
10. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
11. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
12. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry with important references therein, see: (a) Klundt, I. L. Chem. Rev. 1970, 70, 471. (b) Oppolzer, W. Synthesis 1978, 793. (c) Thummel, R. P. Acc. Chem. Res. 1980, 1370. (d) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (e) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P.; Acc. Chem. Res. 1984, 17, 35. (f) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873. (g) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681. (h) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Intl. 1991, 23, 237. (i) Oppolzer, W. Compr. Org. Synth. 1991, 5, 388. (j) Rigby, J. H. Compr. Org. Synth. 1991, 5, 622, 638. (k) Chou, T. Rev. Heteroatom. Chem., Vol. 8; Shigeru, O., Ed.; MYU K.K.: Tokyo, Japan, 1993. (l) Footnote 2 and references therein.
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19. The present results have been communicated in part by Lenihan, B. D.; Shechter, H. Tetrahedron Lett. 1994, 35, 7505.
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35. Silane 7 is obtained in 79% yield using 3 equiv of n-BuLi (Dai-Ho, G.; Mariano, P. S. J. Org. Chem. 1988, 53, 5113) and in 87% yield using 5 equiv of n-BuLi and TMEDA (Lan, A. J. Y.; Heuckeroth, R. O.; Mariano, P. S. J. Am. Chem. Soc. 1987, 109, 2738).
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54. (a) Reaction of dimethyl maleate with α,α′-dimethyl-o-quinodimethane generated by fluoride-induced elimination yields cis-2,3-dicarbomethoxy-1,4-dimethyl-1,2,3,4-tetrahydronaphthalene. The product is formed because the o-quinodimethane cannot undergo 1,5-sigmatropic rearrangement. Cycloaddition of dimethyl maleate to yield the cis adduct also occurs with the unsubstituted o-quinodimethane, which cannot undergo 1,5-sigmatropic rearrangement. Ito, Y.; Nakatsuda, M.; Saegusa, T. J. Am. Chem. Soc. 1982, 104, 7609.
55. (b) Cycloadditions of o-quinonemethide N-alkylimines with fumarate esters give trans-2,3-dicarboalkoxy cycloadducts in good yields, whereas maleate esters give low yields of mixtures of cis- and trans-2,3-dicarboalkoxy cycloadducts in which the trans adducts dominate. Ito, Y.; Nakajo, E.; Saegusa, T. Synth. Commun. 1986, 16, 1073.
56. For reviews of the mechanisms of Diels-Alder reactions, see: (a) Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16. (b) Martin, J. G.; Hill, R. K. Chem. Rev. 1961, 61, 537. (c) Alder, K.; Stein, G. Angew. Chem. 1937, 50, 510. (d) Woodward, R. B.; Baer, H. J. Am. Chem. Soc. 1944, 66, 645. (e) Sauer, J.; Sustmann, R. Angew. Chem. 1980, 92, 773. (f) Van Mele, B.; Huybrechts, G. Int. J. Chem. Kinet. 1989, 21, 967.
57. For reviews of the mechanisms of Diels-Alder reactions, see: (a) Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16. (b) Martin, J. G.; Hill, R. K. Chem. Rev. 1961, 61, 537. (c) Alder, K.; Stein, G. Angew. Chem. 1937, 50, 510. (d) Woodward, R. B.; Baer, H. J. Am. Chem. Soc. 1944, 66, 645. (e) Sauer, J.; Sustmann, R. Angew. Chem. 1980, 92, 773. (f) Van Mele, B.; Huybrechts, G. Int. J. Chem. Kinet. 1989, 21, 967.
58. For reviews of the mechanisms of Diels-Alder reactions, see: (a) Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16. (b) Martin, J. G.; Hill, R. K. Chem. Rev. 1961, 61, 537. (c) Alder, K.; Stein, G. Angew. Chem. 1937, 50, 510. (d) Woodward, R. B.; Baer, H. J. Am. Chem. Soc. 1944, 66, 645. (e) Sauer, J.; Sustmann, R. Angew. Chem. 1980, 92, 773. (f) Van Mele, B.; Huybrechts, G. Int. J. Chem. Kinet. 1989, 21, 967.
59. For reviews of the mechanisms of Diels-Alder reactions, see: (a) Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16. (b) Martin, J. G.; Hill, R. K. Chem. Rev. 1961, 61, 537. (c) Alder, K.; Stein, G. Angew. Chem. 1937, 50, 510. (d) Woodward, R. B.; Baer, H. J. Am. Chem. Soc. 1944, 66, 645. (e) Sauer, J.; Sustmann, R. Angew. Chem. 1980, 92, 773. (f) Van Mele, B.; Huybrechts, G. Int. J. Chem. Kinet. 1989, 21, 967.
60. For reviews of the mechanisms of Diels-Alder reactions, see: (a) Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16. (b) Martin, J. G.; Hill, R. K. Chem. Rev. 1961, 61, 537. (c) Alder, K.; Stein, G. Angew. Chem. 1937, 50, 510. (d) Woodward, R. B.; Baer, H. J. Am. Chem. Soc. 1944, 66, 645. (e) Sauer, J.; Sustmann, R. Angew. Chem. 1980, 92, 773. (f) Van Mele, B.; Huybrechts, G. Int. J. Chem. Kinet. 1989, 21, 967.
61. For reviews of the mechanisms of Diels-Alder reactions, see: (a) Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16. (b) Martin, J. G.; Hill, R. K. Chem. Rev. 1961, 61, 537. (c) Alder, K.; Stein, G. Angew. Chem. 1937, 50, 510. (d) Woodward, R. B.; Baer, H. J. Am. Chem. Soc. 1944, 66, 645. (e) Sauer, J.; Sustmann, R. Angew. Chem. 1980, 92, 773. (f) Van Mele, B.; Huybrechts, G. Int. J. Chem. Kinet. 1989, 21, 967.
62. Shih, C.; Swenton, J. S. J. Org. Chem. 1982, 47, 2668.
63. Allowing the mixture to warm to room temperature without HCl treatment caused formation of a small amount of 22 which is difficult to remove by crystallization.
64. 3 in acetic acid and water oxidizes the 1 Position of tetrahydronaphthalenes. Burnham, J. W.; Duncan, W. P.; Eisenbraun, E. J.; Keen, G. W.; Hamming, M. C. J. Org. Chem. 1974, 39, 1416.
65. Commercial diethyl maleate is contaminated with a small amount of diethyl fumarate. In the present work, the diethyl maleate was purified by chromatography and distillation.
66. Hornback, J. M.; Barrows, R. D. J. Org. Chem. 1982, 47, 4285.