Synthesis of new cyclic homoconjugated oligodiacetylenes

Leibrock B, Vostrowsky O, Hirsch A (2001)


Publication Type: Journal article, Original article

Publication year: 2001

Journal

Original Authors: Leibrock B., Vostrowsky O., Hirsch A.

Publisher: Wiley-VCH Verlag

Pages Range: 4401-4409

Journal Issue: 23

URI: https://www.scopus.com/record/display.uri?eid=2-s2.0-0035215105&origin=inward

Abstract

Cyclic homoconjugated oligodiacetylenes, consisting of butadiyne subunits interconnected with two different sp-linkers in alternation, were synthesized by coupling of different 1,4-pentadiyne synthons. The "exploded" [4]pericyclyne 7 was obtained in a "one-pot" random cyclodehydro-oligomerization reaction, by cross-coupling of two different 1,4-pentadiyne units. Larger ring structures such as the C macrocyclic [6]pericyclyne 22 and the unsymmetrically diynetetrayne expanded C-[4]pericyclyne 27 afforded a stepwise approach. Heterocoupling of two different 1,4-pentadiynes in a molecular ratio of 1:2 and 2:1 afforded the symmetrical pentadecahexaynes 12 and 20, respectively. Cyclodehydrodimerization gave the symmetrically patterned cyclotriacontadodecayne 22. A collective heterocoupling of two different 1,4-pentadiynes with TIPS-acetylene resulted in the formation of acyclic dodecapentayne 26. Final cyclodimerization yielded the cyclotetracosadecayne 27.

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How to cite

APA:

Leibrock, B., Vostrowsky, O., & Hirsch, A. (2001). Synthesis of new cyclic homoconjugated oligodiacetylenes. European Journal of Organic Chemistry, 23, 4401-4409.

MLA:

Leibrock, Bernd, Otto Vostrowsky, and Andreas Hirsch. "Synthesis of new cyclic homoconjugated oligodiacetylenes." European Journal of Organic Chemistry 23 (2001): 4401-4409.

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