RETRACTED: Unclicking the click: mechanically facilitated 1,3-dipolar cycloreversions.

Autor: Brantley JN; Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station A1590, Austin, TX 78712, USA., Wiggins KM, Bielawski CW
Jazyk: angličtina
Zdroj: Science (New York, N.Y.) [Science] 2011 Sep 16; Vol. 333 (6049), pp. 1606-9.
DOI: 10.1126/science.1207934
Abstrakt: The specific targeting of covalent bonds in a local, anisotropic fashion using mechanical methods offers useful opportunities to direct chemical reactivity down otherwise prohibitive pathways. Here, we report that embedding the highly inert 1,2,3-triazole moiety (which is often prepared using the canonical "click" coupling of azides and alkynes) within a poly(methyl acrylate) chain renders it susceptible to ultrasound-induced cycloreversion, as confirmed by comprehensive spectroscopic and chemical analyses. Such reactivity offers the opportunity to develop triazoles as mechanically labile protecting groups or for use in readily accessible materials that respond to mechanical force.
Databáze: MEDLINE