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Volumn 76, Issue 3, 2011, Pages 920-938

Cycloaddition reactions of allenylphosphonates and related allenes with dialkyl acetylenedicarboxylates, 1,3-Diphenylisobenzofuran, and anthracene

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; [4 + 2] CYCLOADDITION; ALLENES; ALLENYLPHOSPHONATE; ARYL GROUP; CARBON-CARBON DOUBLE BONDS; CYCLOADDITION PRODUCTS; CYCLOADDITION REACTION; DIALKYL ACETYLENEDICARBOXYLATES; ENE REACTION; RING CLOSINGS; RING OPENING; SINGLE CRYSTAL X-RAY CRYSTALLOGRAPHY; THERMAL ACTIVATION; VINYL GROUP;

EID: 79851474956     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102240u     Document Type: Article
Times cited : (45)

References (110)
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    • Only the cyclized product was isolated in ca. 25% yield (rest: other productsfrom the reaction of allene (OCH2CMe2CH2O) P-CH=CdCH-2.35 (d, J(H-H̃2.0 Hz, 3H), 3.59-3.66 (m, 2H), 3.88 and 3.90 (2 s, 6H), 4.12-4.16 (m, 2H), 4.13 (d, J(P-H)=22.9 Hz, 1H), 4.16 (br, 1H). 13C NMR (CDCl3): d 17.4, 21.2, 25.5 (d, J(P-C)=134.1 Hz, PCH), 32.3 (d, J(P-C)=5.8 Hz), 52.7 and 52.8 (2 s), 74.9 (d, J(P-C)= 6.3 Hz), 127.9, 133.4, 133.9 Mewith DMAD [mp: 176-178 °C; IR: 1726 cm-1; 1H NMR (CDCl3): d 0.74 and 0.86 (2 s, 6H), 2.35 (d, J(H-H̃2.0 Hz, 3H), 3.59-3.66 (m, 2H), 3.88 and 3.90 (2 s, 6H), 4.12-4.16 (m, 2H), 4.13 (d, J(P-H)=22.9 Hz, 1H), 4.16 (br, 1H). 13C NMR (CDCl3): d 17.4, 21.2, 25.5 (d, J(P-C)=134.1 Hz, PCH), 32.3 (d, J(P-C)=5.8 Hz), 52.7 and 52.8 (2 s), 74.9 (d, J(P-C)= 6.3 Hz), 127.9, 133.4, 133.9, 136.6, 166.8 and 167.5. 31P NMR: d 20.8.].
    • Only the cyclized product was isolated in ca. 25% yield (rest: other productsfrom the reaction of allene (OCH2CMe2CH2O)P-CH=CdCH-2.35 (d, J(H-H̃2.0 Hz, 3H), 3.59-3.66 (m, 2H), 3.88 and 3.90 (2 s, 6H), 4.12-4.16 (m, 2H), 4.13 (d, J(P-H)=22.9 Hz, 1H), 4.16 (br, 1H). 13C NMR (CDCl3): d 17.4, 21.2, 25.5 (d, J(P-C)=134.1 Hz, PCH), 32.3 (d, J(P-C)=5.8 Hz), 52.7 and 52.8 (2 s), 74.9 (d, J(P-C)= 6.3 Hz), 127.9, 133.4, 133.9 Mewith DMAD [mp: 176-178 °C; IR: 1726 cm-1; 1H NMR (CDCl3): d 0.74 and 0.86 (2 s, 6H), 2.35 (d, J(H-H̃2.0 Hz, 3H), 3.59-3.66 (m, 2H), 3.88 and 3.90 (2 s, 6H), 4.12-4.16 (m, 2H), 4.13 (d, J(P-H)=22.9 Hz, 1H), 4.16 (br, 1H). 13C NMR (CDCl3): d 17.4, 21.2, 25.5 (d, J(P-C)=134.1 Hz, PCH), 32.3 (d, J(P-C)=5.8 Hz), 52.7 and 52.8 (2 s), 74.9 (d, J(P-C)= 6.3 Hz), 127.9, 133.4, 133.9, 136.6, 166.8 and 167.5. 31P NMR: d 20.8.].
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    • 2 with DMAD wherein a mixture of Z and E isomers of Me2CdC(C(Me)dCH2)-C(CO2Me)dCH(CO2Mewas obtained. See
    • 2 with DMAD wherein a mixture of Z and E isomers of Me2CdC(C(Me)dCH2)-C(CO2Me)dCH(CO2Mewas obtained. See: Chia, H.-A.; Kirk, B. E.; Taylor, D. R. J. Chem. Soc., Perkin Trans. I 1974, 11, 1209.
    • (1974) J. Chem. Soc., Perkin Trans. I , vol.11 , pp. 1209
    • Chia, H.-A.1    Kirk, B.E.2    Taylor, D.R.3
  • 88
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    • Huisgen and coworkers have reported [4 + 2] cycloaddition using styrene as the diene and 2,2-bis(trifluoromethyl)ethylene-1,1-dicarbonitrile
    • Huisgen and coworkers have reported [4 + 2] cycloaddition using styrene as the diene and 2,2-bis(trifluoromethyl)ethylene-1,1-dicarbonitrile
  • 89
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    • BTFas the dienophile wherein aromaticity is lost in the final compound. This paper also deals with the competition between [4 + 2] and [2 + 2] cycloadditions. See
    • BTFas the dienophile wherein aromaticity is lost in the final compound. This paper also deals with the competition between [4 + 2] and [2 + 2] cycloadditions. See: Brückner, R.; Huisgen, R.; Schmid, J. Tetrahedron Lett. 1990, 31, 7129.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 7129
    • Brückner, R.1    Huisgen, R.2    Schmid, J.3


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