A complete series of eight 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses were subjected to fluorination with DAST. The 1,6:3,4-dianhydropyranoses yielded solely products of skeletal rearrangement resulting from migration of the tetrahydropyran oxygen (educts of D-altro and D-talo configuration) or of the 1,6-anhydro bridge oxygen (D-allo, D-galacto). The major products yielded by the 1,6:2,3...

The thermal stability of a series of dialkylimidazolium carboxylate ionic liquids has been investigated using a broad range of experimental and computational techniques. Ionic liquids incorporating fluoroalkyl carboxylate anions were found to have profoundly differing thermal stabilities and decomposition mechanisms compared with their non-fluorinated analogues. 1-Ethyl-3-methylimidazolium acet...

In nucleophilic aromatic photosubstitution, just as in aromatic substitution in the ground state, substituents can have directing and activating effects. Four rules, which describe orientation of nucleophilic substitution in the excited state, can now be formulated. They are: (a) meta-activation by the nitro group (b) ortho/para-activation by the methoxy group (and probably also by other electr...

Abstract Direct nucleophilic substitution of alcohols with thiols or carbon nucleophiles was achieved using a mesoporous silica‐supported oxovanadium catalyst (VMPS4). Benzyl and allyl were compatible in this reaction under mild conditions, affording the products high yields. The VMPS4 showed excellent chemoselectivity toward presence acid‐labile functional groups, which is contrast to that obs...