Synthesis of h6-(Octahydroacridine)chromiumtricarbonyl Complexes with Non-polar Tails via Molecular Sieves-Catalyzed Cyclization of N-Arylimines and Subsequent Diastereoselective Complexation

Abstract

Molecular sieves catalyzed cyclizations of both various N-arylimines formed in situ from the corresponding arylamines and 3,3,7-trimethyl-6-octenal yielded trans-configurated octahydroacridines.After attachment of non-polar alkyl chains these heterocycles can be complexed diastereoselectively to Cr(C0)3.The products were characterized by X-ray crystal structure determination.The synthesis of amphiphilic metal complexes has received increasing interest due to the unusual chemical and physical properties of the metal center in an ordered biphasic system.' Recent examples are the preparation of Langmuir-Blodgett films from cobalt clusters1 and ferr~cenes,~ the synthesis of watersoluble palladium catalysts,3 rota~anes,~ metallo porphyrin containing vesicles,5 ultrathin polymer films impregnated with redox ~a t a l y s t s , ~ the preparation of Langmuir-Blodgett films from ruthenium(l1)bipyridine complexes7 and monolayers of amphiphilic ferrocenes with NLO properties.8We thus reasoned, whether q6-(octahydroacridine)chromium complexes (1) with long alkyl chains could be prepared diastereoselectively.Recently we reported a highly diastereoselective Lewis acid-catalyzed cyclization of N-arylimines to octahydroacridines9 and their corresponding chromium arene comple~es.'~The reaction can be treated formally as an intramolecular hetero-Diels-Alder reaction1' of a 2-azadiene tethered to a non-activated alkene.In contrast to our previous approach we planned to coordinate the