Download PDF
Synthesis 1999; 1999(1): 100-106
DOI: 10.1055/s-1999-3697
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints All articles of this category

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