Jian-Xin Duan

Synthesis and electrochemical polymerization of new oligothiophene functionalized fluorocyclophanes

New oligothiophene functionalized fluorocyclophanes have been prepared and electropolymerized. The resulting polymers display the classical electroactivity of polythiophenes, showing that the cyclophane ring allows the charge to flow in the polymer. The charge transfer has been shown to be rather similar to that in a functionalized polythiophene, than that in a pendent group polymer.

A simple and efficient method of preparing α-bromo carboxylic acids

Abstract A new and convenient method for α-bromination of aliphatic carboxylic acids is reported. Heating carboxylic acids for 16 hours at 85 °C in trifluoroacetic acid with 1.5 equivalents of N-bromosuccinimide and a catalytic amount of concentrated H 2 SO 4 leads to good yields of the respective α-bromocarboxylic acids.

4,5-Dehydrooctafluoro[2.2]paracyclophane: facile generation and extraordinary Diels-Alder reactivity

Dehydroiodination of 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane by treatment with KOtBu in the presence of benzene, naphthalene, anthracene, or t-butylbenzene affords each of the corresponding Diels–Alder cycloadducts of the presumed aryne intermediate in high yield. The products were characterized by their NMR spectra, with one of them also being confirmed by X-ray crystallography. The extraordinary selectivity/reactivity of the aryne intermediate is discussed.