Affordable Access

deepdyve-link deepdyve-link
Publisher Website

Stereoselective formation of triphenylene ketals.

Authors
  • Boshta, Nader M
  • Bomkamp, Martin
  • Schnakenburg, Gregor
  • Waldvogel, Siegfried R
Type
Published Article
Journal
Chemistry - A European Journal
Publisher
Wiley (John Wiley & Sons)
Publication Date
Mar 15, 2010
Volume
16
Issue
11
Pages
3459–3466
Identifiers
DOI: 10.1002/chem.200903249
PMID: 20157907
Source
Medline
License
Unknown

Abstract

The oxidative trimerization of catechol ketals by MoCl(5) or MoCl(5)/TiCl(4) mixtures leads preferentially to the all-syn stereoisomer of the corresponding triphenylene ketal. The concomitant metal salts of the oxidative coupling most probably form a multinuclear template that directs the diastereoselectivity in a subsequent isomerization step under electrophilic conditions. Several functionalities can serve as coordination sites for the multinuclear metal chloro clusters. Suitable functional groups have to be stable towards the strong electrophilic and oxidizing conditions. Therefore, esters, nitriles, nitro derivatives, triazoles, and pyridines are successfully employed. Based on the flexibility and size of the substrate, different reagent mixtures lead to the stereoselective formation of the all-syn derivatives.

Report this publication

Statistics

Seen <100 times