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Volumn 10, Issue 11, 2008, Pages 2243-2246

1,2-H shift in copper-chlorocarbenoid intermediate during CuCl/bpy-promoted stereoselective dechlorination of 2,2,2-trichloroethyl alkyl ethers to (Z)-1-alkoxy-2-chloroethenes

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EID: 53149085742     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8006524     Document Type: Article
Times cited : (16)

References (27)
  • 14
    • 59849090947 scopus 로고    scopus 로고
    • For the rarity of radical 1,2-H shift in solution, see: (a) Freidlina, R. K.; Kost, V. N.; Khorlina; M. Y., Russ. Chem. Rev. 1962, 31, 1-18.
    • For the rarity of radical 1,2-H shift in solution, see: (a) Freidlina, R. K.; Kost, V. N.; Khorlina; M. Y., Russ. Chem. Rev. 1962, 31, 1-18.
  • 17
    • 59849106062 scopus 로고    scopus 로고
    • The compounds tend to decompose to the corresponding aracyl chlorides on standing in open atmosphere
    • The compounds tend to decompose to the corresponding aracyl chlorides on standing in open atmosphere.
  • 18
    • 85033619792 scopus 로고    scopus 로고
    • 2-promoted reductions, see: (a) Ho, T.-L. Synthesis 1979, 1-20.
    • 2-promoted reductions, see: (a) Ho, T.-L. Synthesis 1979, 1-20.
  • 21
    • 0029022070 scopus 로고
    • For a review, see: a
    • For a review, see: (a) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811-10843.
    • (1995) Tetrahedron , vol.51 , pp. 10811-10843
    • Miller, D.J.1    Moody, C.J.2
  • 22
    • 0035955855 scopus 로고    scopus 로고
    • For some other examples, see: b
    • For some other examples, see: (b) Jiang, N.; Wang, J.; Chan, A. S. C. Tetrahedron Lett. 2001, 42, 8511-8513.
    • (2001) Tetrahedron Lett , vol.42 , pp. 8511-8513
    • Jiang, N.1    Wang, J.2    Chan, A.S.C.3
  • 25
    • 21844480112 scopus 로고    scopus 로고
    • 2-promoted radical cyclization of trihaloethyl allyl/propargyl ethers, see: Nakagawa, M.; Saito, A.; Soga, A.; Yamamoto, N.; Taguchi, T. Tetrahedron Lett. 2005, 46, 5257-5261.
    • 2-promoted radical cyclization of trihaloethyl allyl/propargyl ethers, see: Nakagawa, M.; Saito, A.; Soga, A.; Yamamoto, N.; Taguchi, T. Tetrahedron Lett. 2005, 46, 5257-5261.
  • 27
    • 59849101817 scopus 로고    scopus 로고
    • The copper-carbenoid was generated by the reaction of methyl 2,2-dichloropropanoate with copper powder in DMSO; the only reported example with such a possibility yielded dimerization product (ref 6a).
    • The copper-carbenoid was generated by the reaction of methyl 2,2-dichloropropanoate with copper powder in DMSO; the only reported example with such a possibility yielded dimerization product (ref 6a).


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