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Volumn 49, Issue 41, 2010, Pages 7534-7537

[4+2] cycloaddition reaction of cyclic alkyne-{Co2(CO) 6} complexes with dienes

Author keywords

1,3 dienes; Alkynes; Cobalt; Cycloaddition; Medium sized rings

Indexed keywords

1,3-DIENES; [4 + 2] CYCLOADDITION; [4+2] CYCLOADDITION REACTIONS; ALKYNES; BENZOQUINONES; CYCLIC COMPOUNDS; MEDIUM-SIZED RINGS; PAUSON-KHAND REACTIONS;

EID: 77957562402     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002683     Document Type: Article
Times cited : (11)

References (37)
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    • 8}-catalyzed intramolecular Pauson-Khand reaction of diene-ynes that accompanied [4+2] cycloadditions, however, it seems that the reaction proceeded thermally
    • 8}-catalyzed intramolecular Pauson-Khand reaction of diene-ynes that accompanied [4+2] cycloadditions, however, it seems that the reaction proceeded thermally;
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    • and references therein
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    • For the use of CH3CN as an additive in the Pauson-Khand reaction, see: a)
    • For the use of CH3CN as an additive in the Pauson-Khand reaction, see: a) Y. K. Chung, B. Y. Lee, N. Jeong, M. Hudecek, P. L. Pauson, Organometallics 1993, 12, 220-223;
    • (1993) Organometallics , vol.12 , pp. 220-223
    • Chung, Y.K.1    Lee, B.Y.2    Jeong, N.3    Hudecek, M.4    Pauson, P.L.5
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    • for the Lewis base promoted Pauson-Khand reaction, see: b)
    • for the Lewis base promoted Pauson-Khand reaction, see: b) T. Sugihara, M. Yamaguchi, M. Nishizawa, Chem. Eur. J. 2001, 7, 1589-1595.
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    • For details, see the Supporting Information. We have not been successful in obtaining any obvious decomposition products derived from 1 when the reaction was carried out in the absence of the diene
    • For details, see the Supporting Information. We have not been successful in obtaining any obvious decomposition products derived from 1 when the reaction was carried out in the absence of the diene.
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    • The similar activity of α-oxy and α-methylene substrates (Table 3, entries 5, 6; and 10) compared to that of the α-keto substrate also supports this mechanism
    • The similar activity of α-oxy and α-methylene substrates (Table 3, entries 5, 6; and 10) compared to that of the α-keto substrate also supports this mechanism.
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    • It is likely that a π-allyl intermediate actually exists and retards insertion of CO
    • It is likely that a π-allyl intermediate actually exists and retards insertion of CO.
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    • The regioselectivity of the Pauson-Khand reaction using alkynones or alkynoates as an alkyne component has been examined both experimentally and theoretically to reveal that insertion reaction occurs at the C-Co bond adjacent to the carbonyl group first, see: a)
    • The regioselectivity of the Pauson-Khand reaction using alkynones or alkynoates as an alkyne component has been examined both experimentally and theoretically to reveal that insertion reaction occurs at the C-Co bond adjacent to the carbonyl group first, see: a) T. J. M. de Bruin, C. Michel, K. Vekey, A. E. Greene, Y. Gimbert, A. Milet, J. Organomet. Chem. 2006, 691, 4281;
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    • De Bruin, T.J.M.1    Michel, C.2    Vekey, K.3    Greene, A.E.4    Gimbert, Y.5    Milet, A.6
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    • 6} complex although the yield was low
    • This reversal of regioselectivity was also observed in the reaction of acyclic alkyne-{Co2(CO)6} complex although the yield was low.
  • 37
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    • 6} complex gave benzene derivative in moderate yield
    • 6} complex gave benzene derivative in moderate yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.