6533b82afe1ef96bd128cb4c

RESEARCH PRODUCT

Synthesis of all-syn Functionalized Triphenylene Ketals

Nader M. BoshtaSiegfried R. WaldvogelSiegfried R. WaldvogelGregor SchnakenburgMartin Bomkamp

subject

chemistry.chemical_classificationOrganic ChemistryAcetalSupramolecular chemistryTriphenyleneChemical synthesischemistry.chemical_compoundchemistryHeterocyclic compoundFunctional groupTitanium tetrachlorideOrganic chemistryPhysical and Theoretical ChemistryIsomerization

description

The stereoselective synthesis of triphenylene ketals offers access to unique scaffolds. For a good performance in supramolecular applications an all-syn orientation of the functional groups is essential. The oxidative trimerization of catechol ketals by molybdenum pentachloride or mixtures with titanium tetrachloride leads to a template-directed formation. Several heterocyclic moieties are suitable for this transformation. A template-directed isomerization of anti,anti,syn isomers to the desired C 3 -symmetric derivative was demonstrated in two cases.

yearjournalcountryeditionlanguage
2011-02-21European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.201001699