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Volumn , Issue 7, 2008, Pages 1214-1223

New aldehydes by catalytic diene cycloisomerisations

Author keywords

Aldehydes; Hydroformylation; Isopropylidenecyclohexane; NMR spectroscopy; Stereochemistry

Indexed keywords


EID: 53849127506     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700881     Document Type: Article
Times cited : (7)

References (46)
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    • Eds, P. W. N. M. van Leeuwen, C. Claver, Kluwer Academic Publishers, Dordrecht
    • E. Fernández, S. Castillón in Rhodium Catalysed Hydroformylation (Eds.: P. W. N. M. van Leeuwen, C. Claver), Kluwer Academic Publishers, Dordrecht, 2000, pp. 145-187.
    • (2000) Rhodium Catalysed Hydroformylation , pp. 145-187
    • Fernández, E.1    Castillón, S.2
  • 23
    • 53849086157 scopus 로고    scopus 로고
    • N. Yoshinura, Y. Tokito, E Eur. Pat. 223103, 1987 to Kuraray
    • N. Yoshinura, Y. Tokito, E Eur. Pat. 223103, 1987 (to Kuraray).
  • 33
    • 0004119218 scopus 로고    scopus 로고
    • 2nd ed, Ed, C. S. Sell, RSC Paperbacks, Cambridge
    • c) The Chemistry of Fragrances, 2nd ed. (Ed.: C. S. Sell), RSC Paperbacks, Cambridge, 2006.
    • (2006) The Chemistry of Fragrances
  • 35
    • 53849139744 scopus 로고    scopus 로고
    • The most relevant NOE correlations were those between 3-H and both the methyl group at C-7 and the hydrogen atom trans to the methyl group (Ht). NOE contacts were also observed between 2a-H and both Ht and the methyl group at C-7, as well as between the last two proton signals and the axial methyl group at C-4.
    • The most relevant NOE correlations were those between 3-H and both the methyl group at C-7 and the hydrogen atom trans to the methyl group (Ht). NOE contacts were also observed between 2a-H and both Ht and the methyl group at C-7, as well as between the last two proton signals and the axial methyl group at C-4.
  • 37
    • 53849099296 scopus 로고    scopus 로고
    • 2CHO substituents at C-7 had exchanged their positions with respect to those observed for 1d.
    • 2CHO substituents at C-7 had exchanged their positions with respect to those observed for 1d.
  • 38
    • 53849091315 scopus 로고    scopus 로고
    • This energy calculation was very sensitive to the force field used. Amber force field calculation on 1b gave a population of 70% of conformer A leading to major aldehyde stereoisomer 1d, while with MM2 calculation, the stability of the conformers was reversed, since only 30% of conformer A was present in the equilibrium at the reaction temperature
    • This energy calculation was very sensitive to the force field used. Amber force field calculation on 1b gave a population of 70% of conformer A leading to major aldehyde stereoisomer 1d, while with MM2 calculation, the stability of the conformers was reversed, since only 30% of conformer A was present in the equilibrium at the reaction temperature.
  • 41
    • 53849117076 scopus 로고    scopus 로고
    • [28]), with the Amber force field calculation the amount of this isomer was lowered to 87%, and with MM2 it was only of 45%.
    • [28]), with the Amber force field calculation the amount of this isomer was lowered to 87%, and with MM2 it was only of 45%.
  • 43
    • 53849143242 scopus 로고    scopus 로고
    • 2 group of the ethyl ester of the nitrile derivative 2d appeared as a clear quadruplet pattern, indicating that there is no restriction on the rotation of this fragment. This is in contrast to what was observed for compounds 1d, 1e and 3d with axial carboxylate groups that show nonequivalence of their methylene ester protons.
    • 2 group of the ethyl ester of the nitrile derivative 2d appeared as a clear quadruplet pattern, indicating that there is no restriction on the rotation of this fragment. This is in contrast to what was observed for compounds 1d, 1e and 3d with axial carboxylate groups that show nonequivalence of their methylene ester protons.
  • 44
    • 53849129202 scopus 로고    scopus 로고
    • 13C NMR signals for C-7 and C-8 of the eight major aldehydes prepared appeared in a very narrow range - δ = 21.4 ± 0.5 and 47.4 ± 0.4 ppm, respectively - each about 5 ppm away from the corresponding C-7 and C-8 signals of the minor aldehyde stereoisomers.
    • 13C NMR signals for C-7 and C-8 of the eight major aldehydes prepared appeared in a very narrow range - δ = 21.4 ± 0.5 and 47.4 ± 0.4 ppm, respectively - each about 5 ppm away from the corresponding C-7 and C-8 signals of the minor aldehyde stereoisomers.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.