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Synthesis of alkoxy- and phenylsulfanyl-substituted 1,1-dihalospiro[2.2]pentanes and their reactivity toward methyllithium

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Abstract

A number of new alkoxy- and phenylsulfanyl-substituted 1,1-dihalospiro[2.2]pentanes bearing different halogen atoms were synthesized. 1,1-Dihalo-4-tert-butoxyspiro[2.2]pentanes reacted with methyllithium at −55 to −10°C to give exclusively 1-tert-butoxy-2-vinylidenecyclopropane. The reaction of 1-bromo-1-fluoro-4-phenylsulfanylspiro[2,2]pentane with methyllithium resulted in replacement of the fluorine atom by methyl group.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Leninskie gory 1, Moscow, 119991, Russia

    K. N. Sedenkova, E. B. Averina, I. S. Borisov, Yu. K. Grishin, V. B. Rybakov, T. S. Kuznetsova & N. S. Zefirov

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka, Moscow oblast, Russia

    K. N. Sedenkova, E. B. Averina, T. S. Kuznetsova & N. S. Zefirov

Authors
  1. K. N. Sedenkova
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  2. E. B. Averina
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  3. I. S. Borisov
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  4. Yu. K. Grishin
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  5. V. B. Rybakov
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  6. T. S. Kuznetsova
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  7. N. S. Zefirov
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Corresponding author

Correspondence to E. B. Averina.

Additional information

Original Russian Text © K.N. Sedenkova, E.B. Averina, I.S. Borisov, Yu.K. Grishin, V.B. Rybakov, T.S. Kuznetsova, N.S. Zefirov, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 10, pp. 1271–1277.

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Sedenkova, K.N., Averina, E.B., Borisov, I.S. et al. Synthesis of alkoxy- and phenylsulfanyl-substituted 1,1-dihalospiro[2.2]pentanes and their reactivity toward methyllithium. Russ J Org Chem 48, 1265–1271 (2012). https://doi.org/10.1134/S1070428012100016

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  • DOI: https://doi.org/10.1134/S1070428012100016

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