Get access

Synthesis of pyrimidines from 3-trifluoromethylsulfonyl-oxypropeniminium triflates and nitriles; molecular and crystal structure of the 1:1 and 1:2 Adducts of a 4-(2-diethylaminovinyl)pyrimidine with triflic acid

Authors

  • Rainer Rahm,

    1. Fachbereich Chemie, Universität Kaiserslautern, Erwin-Schrödinger -Straße, D-67663 Kaiserslautern, Germany
    Search for more papers by this author
  • Gerhard Maas

    1. Fachbereich Chemie, Universität Kaiserslautern, Erwin-Schrödinger -Straße, D-67663 Kaiserslautern, Germany
    Current affiliation:
    1. Abteilung Organische Chemie I, Universität Ulm, Albert-Einstein-Allee 11, D-89069 Ulm, Germany
    Search for more papers by this author

  • Dedicated to Professor Richard Neidlein at the occasion of his 65th birthday.

Abstract

The 3-trifluoromethylsulfonyloxy-1-hexeniminium triflate 1 reacts with two equivalents of an aliphatic nitrile or of benzonitrile to give the 4-(2-diethylaminovinyl)pyrimidinediium bis(triflates) 4, which can be deprotonated to give the monoprotonated or neutral pyrimidines 5 and 6, respectively. When the related 1-phenyl-substituted iminium salt 7 is heated in acetonitrile at 140°, 1,5-cyclization of the cation leading to indane derivative 8 competes with formation of the pyrimidinium salt 9. X-ray crystal structure determination reveals significant differences in the bond lengths of mono-and diprotonated 4-(2-diethylaminovinyl)pyrimidines 5a and 4a.

Get access to the full text of this article

Ancillary