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Volumn 77, Issue 15, 2012, Pages 6648-6652

Regioselective and stepwise [8 + 2] cycloaddition reaction between alkynyl-fischer carbene complexes and tropothione

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION; REGIOSELECTIVITY;

EID: 84864619193     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3011304     Document Type: Article
Times cited : (27)

References (46)
  • 28
    • 39749162789 scopus 로고    scopus 로고
    • For a review on [8 + 2] cycloaddition reactions, see: Nair, V.; Abhilash, K. G. Synlett 2008, 301
    • (2008) Synlett , pp. 301
    • Nair, V.1    Abhilash, K.G.2
  • 30
    • 0028815736 scopus 로고
    • 298 = 28.6 kcal/mol) of this process justifies why the reaction of 1g and 2 does not occur at room temperature. In view of this barrier energy, the process might be feasible at higher temperatures. However, tropothione 2 is reported to be thermally unstable. See: Machiguchi, T. Tetrahedron 1995, 51, 1133
    • (1995) Tetrahedron , vol.51 , pp. 1133
    • MacHiguchi, T.1
  • 32
    • 0033591935 scopus 로고    scopus 로고
    • The [3,+1] ring critical point of the electron density has been chosen to compute the NICS values due to its high sensitivity to diamagnetic effects and its unambiguous character. Cossío, F. P.; Morao, I.; Jiao, H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1999, 121, 6737
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 6737
    • Cossío, F.P.1    Morao, I.2    Jiao, H.3    Schleyer V. P, R.4
  • 40
    • 0000695013 scopus 로고
    • Note that bond length equalization in aromatic compounds comes from σ-interactions but not from the π-bonding. The latter would become stronger in bond-alternating geometries: Shaik, S. S.; Bar, R. Nouv. J. Chim. 1984, 8, 411
    • (1984) Nouv. J. Chim. , vol.8 , pp. 411
    • Shaik, S.S.1    Bar, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.