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X-ray structural studies of several novel nitrocyclopropanes

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Abstract

The x-ray crystal structures forcis,cis- andtrans,trans- 2,3-dimethyl-1-nitrocyclopropanecarboxylic acid, 2,2,3,3-tetramethyl-1-nitrocyclopro-panecarbonitrile, 2,2,3,3-tetramethyl-1-nitrocyclo-propanecarboxamide, andtrans,trans,trans,trans-2,2′,3,3′-tetramethyl-1,1′-dinitrobicyclopropyl are reported. Contrary to expectations, π-accepting groups that are syn to dimethyl substituents prefer a conformation perpendicular to the three-membered ring when there is an sp2 electron-withdrawing substituent also bonded to the same carbon atom. Ab initio calculations are reported for model compounds and these results are compared with the experimentally determined ones.

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Authors and Affiliations

  1. Department of Chemistry, University of Pennsylvania, 19104-6323, Philadelphia, PA, USA

    P. E. O'Bannon, Patrick J. Carroll & William P. Dailey

Authors
  1. P. E. O'Bannon
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  2. Patrick J. Carroll
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  3. William P. Dailey
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O'Bannon, P.E., Carroll, P.J. & Dailey, W.P. X-ray structural studies of several novel nitrocyclopropanes. Struct Chem 1, 491–499 (1990). https://doi.org/10.1007/BF00671236

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