Jump to main content
Jump to site search


Three-way competition in topochemical reaction: Permutative azide-alkyne cycloaddition reactions leading to a vast library of products in the crystal

Abstract

5-azido-3-O-propargyl-1,2-O-isopropylidene--D-ribofuranose (1) showed the possibility of topochemical azide-alkyne cycloaddition (TAAC) reaction to form 1,5-triazolyl linked polymers in the crystal. Surprisingly, when thermally activated, the molecules reach a conformational equilibrium wherein the native conformer react intermolecularly to form 1,5-triazolyl-linkage but the other conformer reacts either intermolecularly to form 1,4-triazolyl-linkage or intramolecularly to form 2. Thus TAAC reaction adopts three competing pathways, of which two generate two different types of links for the chain-growth and the third one generates a chain-breaker. While the random occurrence of the chain-breaker reaction ensures the formation of oligomers of different sizes, the permutative occurrence of two types of links in any n-mer produce2n different oligomers of same size.

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 Jan 2018, accepted on 07 Feb 2018 and first published on 07 Feb 2018


Article type: Communication
DOI: 10.1039/C8CE00131F
Citation: CrystEngComm, 2018, Accepted Manuscript
  •   Request permissions

    Three-way competition in topochemical reaction: Permutative azide-alkyne cycloaddition reactions leading to a vast library of products in the crystal

    K. M. Sureshan and K. Hema, CrystEngComm, 2018, Accepted Manuscript , DOI: 10.1039/C8CE00131F

Search articles by author

Spotlight

Advertisements