(E)-1-(Phenylsulfonyl)-4-(trimethylsilyl)-1-butene: An Advantageous Synthetic Equivalent for the 1-(1,3-Butadienyl) Anion and the 1,1-(1,3-Butadienyl) Dianion

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4193-4198

  Meagher, Timothy P ^a   Shechter, Harold ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001428904     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970546c     Document Type: Article

References (36)

1. (a) Hsiao, C.-N.; Shechter, H. Tetrahedron Lett. 1984, 25, 1219.
2. (b) Meagher, T.; Yet, L.; Hsiao, C.-N.; Shechter, H. J. Org. Chem. 1998, 63, 4181.
3. For previous studies of eliminations of vic-trimethylsilyl(phenylsulfonyl) derivatives to olefins, see: (a) Kocienski, P. J. Tetrahedron Lett. 1979, 2649. (b) Kocienski, P. J. J. Org. Chem. 1980, 45, 2037. (c) Hsaio, C.-N.; Shechter, H. Tetrahedron Lett. 1982, 3455. (d) Eisch, J. J.; Behrooz, M.; Dua, S. K. J. Organomet. Chem. 1985, 285, 121. (e) Hsaio, C.-N.; Shechter, H. J. Org. Chem. 1988, 53, 2688. (f) Kim, S. H.; Jin, Z.; Ma, S.; Fuchs, P. L. Tetrahedron Lett. 1995, 4013 and references therein.
4. For previous studies of eliminations of vic-trimethylsilyl(phenylsulfonyl) derivatives to olefins, see: (a) Kocienski, P. J. Tetrahedron Lett. 1979, 2649. (b) Kocienski, P. J. J. Org. Chem. 1980, 45, 2037. (c) Hsaio, C.-N.; Shechter, H. Tetrahedron Lett. 1982, 3455. (d) Eisch, J. J.; Behrooz, M.; Dua, S. K. J. Organomet. Chem. 1985, 285, 121. (e) Hsaio, C.-N.; Shechter, H. J. Org. Chem. 1988, 53, 2688. (f) Kim, S. H.; Jin, Z.; Ma, S.; Fuchs, P. L. Tetrahedron Lett. 1995, 4013 and references therein.
5. For previous studies of eliminations of vic-trimethylsilyl(phenylsulfonyl) derivatives to olefins, see: (a) Kocienski, P. J. Tetrahedron Lett. 1979, 2649. (b) Kocienski, P. J. J. Org. Chem. 1980, 45, 2037. (c) Hsaio, C.-N.; Shechter, H. Tetrahedron Lett. 1982, 3455. (d) Eisch, J. J.; Behrooz, M.; Dua, S. K. J. Organomet. Chem. 1985, 285, 121. (e) Hsaio, C.-N.; Shechter, H. J. Org. Chem. 1988, 53, 2688. (f) Kim, S. H.; Jin, Z.; Ma, S.; Fuchs, P. L. Tetrahedron Lett. 1995, 4013 and references therein.
6. For previous studies of eliminations of vic-trimethylsilyl(phenylsulfonyl) derivatives to olefins, see: (a) Kocienski, P. J. Tetrahedron Lett. 1979, 2649. (b) Kocienski, P. J. J. Org. Chem. 1980, 45, 2037. (c) Hsaio, C.-N.; Shechter, H. Tetrahedron Lett. 1982, 3455. (d) Eisch, J. J.; Behrooz, M.; Dua, S. K. J. Organomet. Chem. 1985, 285, 121. (e) Hsaio, C.-N.; Shechter, H. J. Org. Chem. 1988, 53, 2688. (f) Kim, S. H.; Jin, Z.; Ma, S.; Fuchs, P. L. Tetrahedron Lett. 1995, 4013 and references therein.
7. For previous studies of eliminations of vic-trimethylsilyl(phenylsulfonyl) derivatives to olefins, see: (a) Kocienski, P. J. Tetrahedron Lett. 1979, 2649. (b) Kocienski, P. J. J. Org. Chem. 1980, 45, 2037. (c) Hsaio, C.-N.; Shechter, H. Tetrahedron Lett. 1982, 3455. (d) Eisch, J. J.; Behrooz, M.; Dua, S. K. J. Organomet. Chem. 1985, 285, 121. (e) Hsaio, C.-N.; Shechter, H. J. Org. Chem. 1988, 53, 2688. (f) Kim, S. H.; Jin, Z.; Ma, S.; Fuchs, P. L. Tetrahedron Lett. 1995, 4013 and references therein.
8. For previous studies of eliminations of vic-trimethylsilyl(phenylsulfonyl) derivatives to olefins, see: (a) Kocienski, P. J. Tetrahedron Lett. 1979, 2649. (b) Kocienski, P. J. J. Org. Chem. 1980, 45, 2037. (c) Hsaio, C.-N.; Shechter, H. Tetrahedron Lett. 1982, 3455. (d) Eisch, J. J.; Behrooz, M.; Dua, S. K. J. Organomet. Chem. 1985, 285, 121. (e) Hsaio, C.-N.; Shechter, H. J. Org. Chem. 1988, 53, 2688. (f) Kim, S. H.; Jin, Z.; Ma, S.; Fuchs, P. L. Tetrahedron Lett. 1995, 4013 and references therein.
9. Hauser, C. R.; Hance, C. R. J. Am. Chem. Soc. 1952, 74, 5091.
10. Sommer, L. H.; Goldberg, G. M.; Gold, J.; Whitmore, F. C. J. Am. Chem. Soc. 1947, 69, 980.
11. Weyenberg, D. R.; Toporder, L. H.; Nelson, L. E. J. Org. Chem. 1968, 33, 1975.
12. (a) Sommer, L. H.; Tyler, L. G.; Whitmore, F. C. J. Am. Chem. Soc. 1948, 70, 2872.
13. (b) Salimareeva, I. M.; Zhebarov, O. Z.; Bogatova, N. G.; Yurev, V. P. Zh. Obskch. Khim. 1981, 51, 420.
14. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
15. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
16. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
17. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
18. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
19. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
20. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
21. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
22. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
23. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
24. For previous examples of such additions, see: (a) Cristol, S. J.; Reeder, J. A. J. Org. Chem. 1961, 26, 2182. (b) Vasil'eva, M. A.; Bychkova, T. I.; Kushnarev, D. F.; Rozova, T. I.; Kalabina, A. V. Zh. Org. Khim. 1977, 13, 283. (c) Asscher, M.; Vofsi, D. J. Chem Soc. 1964, 4962. (d) Amiel, Y. Tetrahedron Lett. 1971, 661. (e) Yoshiaki, K.; Muria, S.; Sonoda, N.; Tsutsumi, S. Organomet. Chem. Synth. 1972, 1, 465. (f) Dunoques, J.; Pillot, J.-P.; Duffaut, N.; Calas, R. C. R. Acad. Sci. Ser. C 1974, 278, 467. (g) Pillot, J. P.; Dunoques, J.; Calas, R. Synthesis 1977, 469. (h) Zakharkin, L. I.; Zhigareva, G. C. Zh. Org. Khim. 1973, 9, 891. Boll, W. Liebigs Ann. Chim. 1979, 1655. (i) Kalabina, A. V.; Vasil'eva, M. A.; Bychkova, T. I. Zh. Org. Khim. 1979, 75, 268. (j) Doomes, E.; Clarke, U.; Neitzel, J. J. Org. Chem. 1987, 52, 1540.
25. An alternate method for preparing 11, 22, and 23 which has not been evaluated in this work is addition of arylsulfenyl chlorides to 10 followed by oxidation with percarboxylic acids: Hopkins, P. B.; Fuchs, P. L. J. Org. Chem. 1978, 43, 1208.
26. 9b
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