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Synthesis 1999; 1999(1): 100-106
DOI: 10.1055/s-1999-3697
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Propyne Iminium Salts By N-Alkylation of Alkynyl Imines

Jens Schlegel* , Gerhard Maas
  • *Abteilung Organische Chemie I, Universität Ulm, Albert-Einstein-Allee 11, D-89081 Ulm, Germany; Fax +49(7 31)5 02 28 03; E-mail: gerhard.maas@chemie.uni-ulm.de
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Publication Date:
31 December 1999 (online)

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N-Alkylation of alkynyl imines 5, 6, and 8 with methyl triflate or triethyloxonium tetrafluoroborate provides the open-chain propyne iminium salts 9 and 10, the related salts 11a-e and 12b where the iminium function is a part of a heteroaromatic ring, and p-phenylene-bis(propyne iminium) salts 13a,c. The method gives access to novel propyne iminium salts in which the C,C triple bond bears an alkyl, SiMe3, or H substituent.

alkynyl imines - iminium salts - imine alkylation - imidoyl halides - C,C coupling with alkynes

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