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Orientation in the metalation of amide, carbamate, ureido, and allylic derivatives of cymantrene

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Abstract

The orientation in the metalation of monosubstituted carbamate-, amide-, ureido-, and allyl-containing derivatives of cymantrene was determined for the first time. The data obtained open up a synthetic route to polyfunctional 1,2- and 1,3-disubstituted cymantrenes. They can serve as the starting materials for the preparation of chelate complexes of (dicarbonyl)-(cyclopentadienyl)manganese, which hold promise as novel organometallic photochromes. A method for the synthesis of earlier unknown chiral derivatives of cymantrene with a quaternary carbon atom in position 1 of the side chain was proposed.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    E. S. Kelbysheva, L. N. Telegina, I. A. Godovikov, T. V. Strelkova, A. F. Smol’yakov, F. M. Dolgushin & N. M. Loim

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  1. E. S. Kelbysheva
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  2. L. N. Telegina
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  3. I. A. Godovikov
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  4. T. V. Strelkova
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  5. A. F. Smol’yakov
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  6. F. M. Dolgushin
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  7. N. M. Loim
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Correspondence to N. M. Loim.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2304–2315, December, 2012.

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Kelbysheva, E.S., Telegina, L.N., Godovikov, I.A. et al. Orientation in the metalation of amide, carbamate, ureido, and allylic derivatives of cymantrene. Russ Chem Bull 61, 2326–2337 (2012). https://doi.org/10.1007/s11172-012-0327-8

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  • DOI: https://doi.org/10.1007/s11172-012-0327-8

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