Mechanistic studies on the rearrangement of 1-alkenyl-2-alkynylcyclopropanes: From allylic gold(I) cations to stable carbocations

  1. Tudela, Eva . 1
  2. González, Jairo. 1
  3. Vicente, R. 1
  4. Santamaría, J. 1
  5. Rodríguez, M.A. 2
  6. Ballesteros, A. 1
  1. 1 Universidad de Oviedo
    info

    Universidad de Oviedo

    Oviedo, España

    ROR https://ror.org/006gksa02

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Angewandte Chemie International

ISSN: 1433-7851

Any de publicació: 2014

Volum: 53

Número: 45

Pàgines: 12097-12100

Tipus: Article

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DOI: 10.1002/ANIE.201407055 SCOPUS: 2-s2.0-84941085097 WoS: WOS:000344052000015 GOOGLE SCHOLAR

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Resum

An allylic gold(I) cation, proposed as key intermediate in the gold-promoted rearrangement of 1,5-enynes bearing a fixed conformation, has been detected and characterized by NMR spectroscopy. Moreover, its participation in the overall transformation was confirmed. Computational studies indicate that the gold-catalyzed transformation occurs through an uncommon rearrangement. Additionally, this study led us to isolate and characterize a stable homoantiaromatic carbocation.