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Volumn 44, Issue 13, 2005, Pages 2008-2011

Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride

Author keywords

Carbenes; Chromium; Isotopic labeling; Rearrangement; Synthetic methods

Indexed keywords

ALCOHOLS; AROMATIC COMPOUNDS; ETHERS; HYDROGEN; OLEFINS; REACTION KINETICS; REDUCTION;

EID: 16844375730     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461884     Document Type: Article
Times cited : (37)

References (30)
  • 2
    • 0035794912 scopus 로고    scopus 로고
    • a) J. R. Falck, D. K. Barma, R. Baati, C. Mioskowski, Angew. Chem. 2001, 113, 1321; Angew. Chem. Int. Ed. 2001, 40, 1281;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1281
  • 7
    • 0034600784 scopus 로고    scopus 로고
    • M. Bandini, P. G. Cozzi, A. Umani-Ronchi, Angew. Chem. 2000, 112, 2417; Angew. Chem. Int. Ed. 2000, 39, 2327.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2327
  • 8
    • 0141741260 scopus 로고    scopus 로고
    • 2,2,2-Trichloroethyl esters undergo rearrangement to 1-halovinyl esters through a radical pathway known as a Surzur-Tanner rearrangement with a mixture of CuCl and bipyridine (1:1). See: R. N. Ram, N. K. Meher, Org. Lett. 2003, 5, 145.
    • (2003) Org. Lett. , vol.5 , pp. 145
    • Ram, R.N.1    Meher, N.K.2
  • 13
    • 16844368495 scopus 로고    scopus 로고
    • 1H NMR spectroscopy. The stereochemistry of 2e could not be determined by spectroscopy, but by analogy with the other compounds it is assumed that (Z)-2e is obtained.
  • 15
    • 16844364047 scopus 로고    scopus 로고
    • note
    • 1H nOe NMR spectroscopy.
  • 19
    • 33845471004 scopus 로고
    • The organochromium species undergo a rehybridization by placing a positive charge in a p orbital to produce a tight ion pair: a) H. M. Walborsky, M. Duraisamy, J. Am. Chem. Soc. 1984, 106, 5035; b) H. M. Walborsky, J. Rachon, V. Goedken, J. Am. Chem. Soc. 1986, 108, 7435.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 5035
    • Walborsky, H.M.1    Duraisamy, M.2
  • 20
    • 33845376318 scopus 로고
    • The organochromium species undergo a rehybridization by placing a positive charge in a p orbital to produce a tight ion pair: a) H. M. Walborsky, M. Duraisamy, J. Am. Chem. Soc. 1984, 106, 5035; b) H. M. Walborsky, J. Rachon, V. Goedken, J. Am. Chem. Soc. 1986, 108, 7435.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7435
    • Walborsky, H.M.1    Rachon, J.2    Goedken, V.3
  • 22
    • 0001455738 scopus 로고
    • 2X. However, this mechanism is unlikely as the formation of 2f (Table 1, entry 7) would require rearrangement to a quaternary center. For a review of the dyotropic rearrangement, see: M. T. Reetz, Tetrahedron 1973, 29, 2189.
    • (1973) Tetrahedron , vol.29 , pp. 2189
    • Reetz, M.T.1
  • 25
    • 0000096360 scopus 로고
    • 2O. See: a) P. L. Creger, J. Am. Chem. Soc. 1970, 92, 1396; b) D. Seebach, M. Boes, R. Naef, W. B. Schweizer, J. Am. Chem. Soc. 1983, 105, 5390.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 1396
    • Creger, P.L.1
  • 27
    • 16844371030 scopus 로고    scopus 로고
    • note
    • The fragmentation of β-sulfonate- and β-phosphate-substituted alkyl radicals is known to compete with the Surzur-Tanner rearrangement. See ref. [13].
  • 28
    • 0026752426 scopus 로고
    • The starting 2-alkoxy-substituted 1,1,1-trihaloalkanes were prepared according to: a) E. J. Corey, J. O. Link, Y. Shao, Tetrahedron Lett. 1992, 33, 3435; b) J. Russell, N. Roques, Tetrahedron 1998, 54, 13771; c) M. Shimizu, N. Yamada, Y. Takebe, T. Hata, M. Kuroboshi, T. Tamejiro Hiyama, Bull. Chem. Soc. Jpn. 1998, 71, 2903.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3435
    • Corey, E.J.1    Link, J.O.2    Shao, Y.3
  • 29
    • 0032487852 scopus 로고    scopus 로고
    • The starting 2-alkoxy-substituted 1,1,1-trihaloalkanes were prepared according to: a) E. J. Corey, J. O. Link, Y. Shao, Tetrahedron Lett. 1992, 33, 3435; b) J. Russell, N. Roques, Tetrahedron 1998, 54, 13771; c) M. Shimizu, N. Yamada, Y. Takebe, T. Hata, M. Kuroboshi, T. Tamejiro Hiyama, Bull. Chem. Soc. Jpn. 1998, 71, 2903.
    • (1998) Tetrahedron , vol.54 , pp. 13771
    • Russell, J.1    Roques, N.2
  • 30
    • 0032442654 scopus 로고    scopus 로고
    • The starting 2-alkoxy-substituted 1,1,1-trihaloalkanes were prepared according to: a) E. J. Corey, J. O. Link, Y. Shao, Tetrahedron Lett. 1992, 33, 3435; b) J. Russell, N. Roques, Tetrahedron 1998, 54, 13771; c) M. Shimizu, N. Yamada, Y. Takebe, T. Hata, M. Kuroboshi, T. Tamejiro Hiyama, Bull. Chem. Soc. Jpn. 1998, 71, 2903.
    • (1998) Bull. Chem. Soc. Jpn. , vol.71 , pp. 2903
    • Shimizu, M.1    Yamada, N.2    Takebe, Y.3    Hata, T.4    Kuroboshi, M.5    Tamejiro Hiyama, T.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.