This communication reports on the utility of a triazine-based self-assembling system, reminiscent of a Janus G−C nucleobase, as a building block for developing (1) supramolecular polymers, (2) peptide nucleic acids (PNAs), and (3) smart polymers. The strategically positioned self-complementary triple H-bonding arrays DDA and AAD facilitate efficient self-assembly, leading to a linear supramolecular polymer.
An oxa-[2,3] sigmatropic rearrangement
involving arynes is reported
featuring the umpolung of ketones, where the CO bond polarity
is reversed. The in situ-generated sulfur ylides from β-keto
thioethers and arynes undergo efficient rearrangement allowing the
facile and robust synthesis of functionalized enol ethers in high
yields and excellent functional group compatibility. Preliminary mechanistic
studies rule out the possibility of Pummerer-type rearrangement operating
in this case.
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