Synthesis of  all ‐ syn  Functionalized Triphenylene Ketals | Zendy

Boshta Nader M. | Zendy; Bomkamp Martin | Zendy; Schnakenburg Gregor | Zendy; Waldvogel Siegfried R. | Zendy

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Synthesis of all ‐ syn Functionalized Triphenylene Ketals

Author(s) -

Boshta Nader M.,

Bomkamp Martin,

Schnakenburg Gregor,

Waldvogel Siegfried R.

Publication year - 2011

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201001699

Subject(s) - triphenylene , chemistry , catechol , derivative (finance) , stereoselectivity , isomerization , supramolecular chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , molecule , financial economics , economics

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.

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