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Volumn 75, Issue 1, 2010, Pages 249-252

O-Nitrophenyl sulfoxides: Efficient precursors for the mild preparation of alkenes

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; HIGH PURITY; SIMULTANEOUS PRECIPITATION; SULFENIC ACIDS; SYNTHETIC PRECURSORS; TERMINAL ALKENES; THERMOLYTIC CONDITIONS;

EID: 73449088733     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902248z     Document Type: Article
Times cited : (11)

References (18)
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    • (a) Cope, A. C.; Foster, T. T.; Towle, P. H. J. Am. Chem. Soc. 1949, 71, 3929-3934. (b) DePuy, C. H.; King, R. W. Chem. Rev. 1960, 60, 431-457.
  • 5
    • 73449093669 scopus 로고    scopus 로고
    • Bamford, W. R.; Stevens, T. S. J. Chem. Soc. 1952, 4735-4750. (b) Shapiro, R. H..; et al. Org. React. 1976, 23, 405-507.(c) Adlington, R. M.; Barrett, A. G. M. Acc. Chem. Res. 1983, 16, 55-59.
    • (a) Bamford, W. R.; Stevens, T. S. J. Chem. Soc. 1952, 4735-4750. (b) Shapiro, R. H..; et al. Org. React. 1976, 23, 405-507.(c) Adlington, R. M.; Barrett, A. G. M. Acc. Chem. Res. 1983, 16, 55-59.
  • 6
    • 73449135653 scopus 로고    scopus 로고
    • Chugaev, L. Ber. Dtsch. Chem. Ges. 1899, 32, 3332-3335. (b) Nace, H. R. Org. React. 1962, 12, 57-100.
    • (a) Chugaev, L. Ber. Dtsch. Chem. Ges. 1899, 32, 3332-3335. (b) Nace, H. R. Org. React. 1962, 12, 57-100.
  • 9
    • 73449090612 scopus 로고    scopus 로고
    • Field, L. Synthesis 1972, 101-133. (b) Field, L. Synthesis 1978, 713-740. (c) Trost, B. M.; Salzman, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887-4902. (d) Trost, B. M. Acc. Chem. Res. 1978, 11, 453-461. (e) Trost, B. M. Chem. Rev. 1978, 78, 363-382.
    • (a) Field, L. Synthesis 1972, 101-133. (b) Field, L. Synthesis 1978, 713-740. (c) Trost, B. M.; Salzman, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887-4902. (d) Trost, B. M. Acc. Chem. Res. 1978, 11, 453-461. (e) Trost, B. M. Chem. Rev. 1978, 78, 363-382.
  • 12
    • 73449138089 scopus 로고    scopus 로고
    • The trans selectivity for ester (E)-5c was believed to be due to an unfavorable interaction between the benzyl ester and methyl in the transition state of the cis product. (Chemical Equation Presented)
    • The trans selectivity for ester (E)-5c was believed to be due to an unfavorable interaction between the benzyl ester and methyl in the transition state of the cis product. (Chemical Equation Presented)
  • 13
    • 73449084643 scopus 로고    scopus 로고
    • Yoshimura, T.; Tsukurimichi, E.; Iizuka, K.; Mizuno, H.; Isaji, H.; Shimasaki, C. Bull. Chem. Soc. Jpn. 1989, 62, 1891-1899. (b) Emerson, D. W.; Korniski, T. J. J. Org. Chem. 1969, 34, 4115-4118.
    • (a) Yoshimura, T.; Tsukurimichi, E.; Iizuka, K.; Mizuno, H.; Isaji, H.; Shimasaki, C. Bull. Chem. Soc. Jpn. 1989, 62, 1891-1899. (b) Emerson, D. W.; Korniski, T. J. J. Org. Chem. 1969, 34, 4115-4118.
  • 14
    • 73449119106 scopus 로고    scopus 로고
    • Catozzi, N.; Edwards, M. G.; Raw, S. A.; Wasnaire, P.; Taylor, R. J. K. J. Org. Chem. 2009, 74, 8343-8354. (b) Matsuo, J.; Kawano, M.; Takeuchi, K.; Tanaka, H.; Ishibashi, H. Tetrahedron Lett. 2009, 50, 1917-1919. (c) Simila, S. T. M.; Martin, S. F. Tetrahedron Lett. 2008, 49, 4501-4504. (d) Ishibashi, H.; Kato, I.; Takeda, Y.; Kogure, M.; Tamura, O. Chem. Commun. 2000, 16, 1527-1528. (e) Mash, E. A.; Gregg, T. M. J. Org. Chem. 1995, 60, 6180-6182. (f) Zonjee, J. N.; De Koning, H.; Speckamp, W. Tetrahedron 1989, 45, 7553-7564.
    • (a) Catozzi, N.; Edwards, M. G.; Raw, S. A.; Wasnaire, P.; Taylor, R. J. K. J. Org. Chem. 2009, 74, 8343-8354. (b) Matsuo, J.; Kawano, M.; Takeuchi, K.; Tanaka, H.; Ishibashi, H. Tetrahedron Lett. 2009, 50, 1917-1919. (c) Simila, S. T. M.; Martin, S. F. Tetrahedron Lett. 2008, 49, 4501-4504. (d) Ishibashi, H.; Kato, I.; Takeda, Y.; Kogure, M.; Tamura, O. Chem. Commun. 2000, 16, 1527-1528. (e) Mash, E. A.; Gregg, T. M. J. Org. Chem. 1995, 60, 6180-6182. (f) Zonjee, J. N.; De Koning, H.; Speckamp, W. Tetrahedron 1989, 45, 7553-7564.
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    • Ishibashi, H.; Komatsu, H.; Maruyama, K.; Ikeda, M. Tetrahedron Lett. 1985, 26, 5791-5794. (b) Ishibashi, H.; Komatsu, H.; Ikeda, M. J. Chem. Res., Synop. 1987, 9, 296-297.
    • (a) Ishibashi, H.; Komatsu, H.; Maruyama, K.; Ikeda, M. Tetrahedron Lett. 1985, 26, 5791-5794. (b) Ishibashi, H.; Komatsu, H.; Ikeda, M. J. Chem. Res., Synop. 1987, 9, 296-297.


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