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Volumn , Issue 26, 2009, Pages 4395-4399

Unusual behavior of the anionic species from (E)-1-chloro-3,3,3- trifluoropropene(HCFC-1233t)

Author keywords

Alcohols; Alkenes; Fluorine; Rearrangement

Indexed keywords


EID: 69449091857     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900370     Document Type: Article
Times cited : (12)

References (47)
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    • (Honeywell International), U. S. Pat. Appl. Publ. 2005020862
    • e) H.-S. Tung, R. C. Johnson, D. C. Merkel (Honeywell International), U. S. Pat. Appl. Publ. 2005020862, 2005;
    • (2005)
    • Tung, H.-S.1    Johnson, R.C.2    Merkel, D.C.3
  • 28
    • 69449104269 scopus 로고    scopus 로고
    • Since 2 equiv. of a base is required for the formation of 4e on the basis of the reaction mechanism shown in Scheme 1, 60% is the theoretical yield
    • Since 2 equiv. of a base is required for the formation of 4e on the basis of the reaction mechanism shown in Scheme 1, 60% is the theoretical yield.
  • 29
    • 69449090341 scopus 로고
    • Each point was obtained by performing the experiments 2-3 times. MeLi was titrated by a literature method See: (Ed.: M. Schlosser), John Wiley & Sons, New York, ch. 4
    • Each point was obtained by performing the experiments 2-3 times. MeLi was titrated by a literature methodSee: B. H Lipshutz in Organometallics in Synthesis A Manual (Ed.: M. Schlosser), John Wiley & Sons, New York, 1994, ch. 4, pp. 283382.
    • (1994) Organometallics in Synthesis A Manual , pp. 283382
    • Lipshutz, B.H.1
  • 30
    • 69449094076 scopus 로고    scopus 로고
    • Judging from Table 1, because LDA behaved basically in a similar manner to MeLi at least in THF and spontaneous reaction was readily expected by mixing MeLi and PhCHO, we selected the former base here
    • Judging from Table 1, because LDA behaved basically in a similar manner to MeLi at least in THF and spontaneous reaction was readily expected by mixing MeLi and PhCHO, we selected the former base here.
  • 32
    • 69449108114 scopus 로고    scopus 로고
    • This is the species actually obtained by DFT optimization
    • This is the species actually obtained by DFT optimization.
  • 33
    • 69449088547 scopus 로고    scopus 로고
    • Clear pictures of their structures have not been obtained yet
    • Clear pictures of their structures have not been obtained yet.
  • 37
    • 45949126715 scopus 로고    scopus 로고
    • For the similar species with zinc instead of Li, see, S. W Hansen, T. D. Spawn, D. J. Burton, J. Fluorine Chem. 1987, 35, 415-420.
    • J. Fluorine Chem. , vol.1987 , Issue.35 , pp. 415-420
  • 39
    • 4644275985 scopus 로고    scopus 로고
    • b) R. Knorr, Chem. Rev. 2004,104, 3795-3849.
    • (2004) Chem. Rev. , vol.104 , pp. 3795-3849
    • Knorr, R.1
  • 40
    • 69449100693 scopus 로고    scopus 로고
    • One of the referees pointed out the possible equilibration between Int-1 and Int-2 in the presence of (E)-1, whereas our experiment proved that this was not the case: To a solution of (E)-1 was added MeLi (1.2 equiv.) at -80 °C and after 0.5 h, another 0.8 equiv. of MeLi was added. When 2 equiv. of MeLi was added all at once, (E)-2e was afforded in excellent selectivity by the addition of PhCHO (see Entry 15 in Table land Figure 1), whereas what was actually obtained was 4e only in 68 % yield
    • One of the referees pointed out the possible equilibration between Int-1 and Int-2 in the presence of (E)-1, whereas our experiment proved that this was not the case: To a solution of (E)-1 was added MeLi (1.2 equiv.) at -80 °C and after 0.5 h, another 0.8 equiv. of MeLi was added. When 2 equiv. of MeLi was added all at once, (E)-2e was afforded in excellent selectivity by the addition of PhCHO (see Entry 15 in Table land Figure 1), whereas what was actually obtained was 4e only in 68 % yield.
  • 41
    • 0000517236 scopus 로고
    • C=C was reported to rearrange into acetylene within a period of picoseconds
    • 2
    • 2C=C was reported to rearrange into acetylene within a period of picoseconds. G. A. Petersson, T. G. Tensfeldt, J. A. Montgomery Jr, J. Am. Chem. Soc. 1992, 114, 6133-6138.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6133-6138
    • Petersson, G.A.1    Tensfeldt, T.G.2    Montgomery Jr, J.A.3
  • 44
    • 69449100821 scopus 로고    scopus 로고
    • The original procedure, mixing 4 equiv. of piperidine with (E)1 at 0 °C for 3 h, allowed the isolation of (E)-6a in 73% yield.
    • The original procedure, mixing 4 equiv. of piperidine with (E)1 at 0 °C for 3 h, allowed the isolation of (E)-6a in 73% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.