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Unusual selective allylation of norbornadiene in the presence of palladium nanoclusters

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Russian Chemical Bulletin Aims and scope

Abstract

The reaction of norbornadiene (NBD) with allyl acetate in the presence of the nanocluster Pd147phen32O60(OCOBut)30 (Pd-147; phen is 1,10-phenanthroline) and PPh3 in acetonitrile is nonselective and is accompanied by the decomposition of the cluster, affording the same allylation products of NBD as the reaction with Pd3(OAc)6 or Pd(dba)2 (dba is dibenzylideneacetone) combined with PPh3. In contrast, in the ionic liquid [bmim][BF4] (bmim is 1-butyl-3-methylimidazolinium), the Pd-147 is not decomposed and the reaction occurs selectively to give methylidene(vinyl)norbornene as the sole product. The data obtained suggest that in an ionic liquid, the reaction under study is catalyzed by the nanocluster Pd-147 rather than by the products of its decomposition.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, 86 prosp. Vernadskogo, 117571 Moscow, Russian Federation, Russia

    E. M. Evstigneeva, O. S. Manulik & V. R. Flid

  2. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninskii prosp., 119991 Moscow, Russian Federation, Russia

    I. P. Stolyarov, N. Yu. Kozitsyna, M. N. Vargaftik & I. I. Moiseev

Authors
  1. E. M. Evstigneeva
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  2. O. S. Manulik
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  3. V. R. Flid
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  4. I. P. Stolyarov
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  5. N. Yu. Kozitsyna
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  6. M. N. Vargaftik
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  7. I. I. Moiseev
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Evstigneeva, E.M., Manulik, O.S., Flid, V.R. et al. Unusual selective allylation of norbornadiene in the presence of palladium nanoclusters. Russian Chemical Bulletin 53, 1345–1348 (2004). https://doi.org/10.1023/B:RUCB.0000042298.81687.dd

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