Synlett 2002(12): 1939-1953
DOI: 10.1055/s-2002-35578
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Cross-Conjugated Oligo(enynes)

Rik R. Tykwinski*, Yuming Zhao
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada
Fax: +11(780)4928231; e-Mail: rik.tykwinski@ualberta.ca;
Weitere Informationen

Publikationsverlauf

Received 27 November 2001
Publikationsdatum:
20. November 2002 (online)

Abstract

Synthetic efforts toward cross-conjugated enyne oligomers are detailed in this account. This includes the realization of iso-polydiacetylenes (iso-PDAs) and iso-polytriacetylenes (iso-PTAs), the cross-conjugated constitutional isomers of polydiacetyl­enes and polytriacetylenes, respectively. These compounds can be readily accessed via palladium-catalyzed cross-coupling reactions between vinyl triflates and terminal alkynes, or oxidative acetylenic coupling of terminal alkynes using Hay methodology. Electronic communication along the π-framework of these oligomers is described as a function of both oligomer length and terminal substitution.

  • 1 Introduction

  • 2 iso-Polydiacetylenes

  • 3 iso-Polytriacetylenes and Beyond

  • 4 Donor-Acceptor Derivatives of Cross-Conjugated Enynes

  • 5 Conclusions and Perspectives

25

Eisler, S.; Tykwinski, R. R. unpublished results.

29

Zhao, Y.; Tykwinski, R. R. unpublished results.