Isomerisation of alpha-pinene oxide in the presence of indenyl allyl dicarbonyl molybdenum(II) and tungsten(II) complexes

abstract

The indenyl complexes IndM(eta(3)-C3H5)(CO)(2) (M= Mo (1), W (2)), (IndMe)Mo(eta(3)-C3H5)(CO)(2) (3) and (IndSiMe(3))Mo(eta(3)-C3H5)(Co)(2) (4) display catalytic activity for the isomerisation of alpha-pinene oxide. Conversion reached 97% after 3 h at 35 degrees C in the presence of 1 and 1,2-dichloroethane as solvent, giving campholenic aldehyde in 56% yield. Solvent polarity and basicity appear to affect the reaction rate. Whereas the type of substituent on the indenyl ligand does not appear to have a strong impact on catalytic performance, changing the metal centre from Mo (1) to W (2) gave a significantly more active catalyst. (C) 2012 Elsevier B.V. All rights reserved.

keywords

MEINWALD REARRANGEMENT REACTIONS; ORGANOMETALLIC LEWIS-ACIDS; PI-ALLYL; MIXED-RING; CATALYSTS; PRECURSORS; TETRAFLUOROBORATE; TRANSFORMATIONS; TUNGSTENOCENE; MOLYBDENOCENE

subject category

Chemistry

authors

Bruno, SM; Gamelas, CA; Gomes, AC; Valente, AA; Pillinger, M; Romao, CC; Goncalves, IS

our authors

acknowledgements

We are grateful to the Fundacao para a Ciencia e a Tecnologia (FCT), the Programa Operacional Ciencia e Inovacao (POCI) 2010, Orcamento do Estado (OE), Fundo Europeu de Desenvolvimento Regional (FEDER) and CICECO (Pest-C/CTM/LA0011/2011) for financial support. The FCT and the European Social Fund are acknowledged for a post-doctoral grant to S.M.B. (SFRH/BPD/46473/2008).

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