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Volumn 16, Issue 28, 2010, Pages 8255-8258

Nucleophilic silylenoid character of stable phosphonium sila-ylides

Author keywords

Cycloaddition; Phosphorus; Silicon; Silylenes; Ylides

Indexed keywords

CARBONYL COMPOUNDS; DONOR-ACCEPTORS; LOW ENERGIES; SILYLENES; SILYLENOIDS;

EID: 77954847533     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001054     Document Type: Article
Times cited : (40)

References (46)
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  • 18
  • 24
    • 76149141855 scopus 로고    scopus 로고
    • Two types of mechanisms have been proposed, either through a silacyclopropene intermediate by a [2+1] cycloaddition or through a zwitterionic species by a nucleophilic attack, of sila-ylide on the alkyne respectively, see: a) S. S. Sen, H. W. Roesky, D. Stern, J. Henn, D. Stalke, J. Am. Chem. Soc. 2010, 132, 1123;
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 1123
    • Sen, S.S.1    Roesky, H.W.2    Stern, D.3    Henn, J.4    Stalke, D.5
  • 27
    • 77954839987 scopus 로고    scopus 로고
    • The diastereoselectivity of the reaction was indicated by the formation of diastereomers 2 in the same proportions as those observed for the starting ylide 1 (85:15).
    • The diastereoselectivity of the reaction was indicated by the formation of diastereomers 2 in the same proportions as those observed for the starting ylide 1 (85:15).
  • 29
    • 0032578195 scopus 로고    scopus 로고
    • Only two pentacoordinate silicon-containing three-membered rings are known to date, see: a) N. W. Mitzel, U. Losehand, J. Am. Chem. Soc. 1998, 120, 7320;
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7320
    • Mitzel, N.W.1    Losehand, U.2
  • 32
    • 77954842046 scopus 로고    scopus 로고
    • CCDC-766291 (2) and 766292 (8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 36
    • 77954841652 scopus 로고    scopus 로고
    • -1). See Scheme Sl of the Supporting Information.
    • -1). See Scheme Sl of the Supporting Information.
  • 37
    • 77954843241 scopus 로고    scopus 로고
    • -1 (4c)).
    • -1 (4c)).
  • 38
    • 0035913753 scopus 로고    scopus 로고
    • The α, β-ambiphilic reactivity of phosphonium sila-ylides with acetylenes was postulated, see: A. Toshimitsu; T. Saeki, K. Tamao, J. Am. Chem. Soc. 2001, 123, 9210-9211.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9210-9211
    • Toshimitsu, A.1    Saeki, T.2    Tamao, K.3
  • 40
    • 31544461484 scopus 로고    scopus 로고
    • (Ed.: P.J. Murphy), Oxford University Press, Oxford
    • b) A. D. Abell, M. K. Edmonds Organophosphorus Reagents (Ed.: P.J. Murphy), Oxford University Press, Oxford, 2004, p. 99.
    • (2004) Organophosphorus Reagents , pp. 99
    • Abell, A.D.1    Edmonds, M.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.