title: Photochemical synthesis of N-adamantylhomoallylamines through addition of cyclic olefins to imines catalyzed by alumina grafted cadmium sulfide.
abstract: Grafting cadmium sulfide onto alumina induces a small bandgap widening and a more significant lifetime variation of the light generated charge carriers from 0.76 microseconds measured for pristine CdS to 0.75, 0.86, and 1.20 microseconds found for CdS/Al(2)O(3) containing 30, 20, and 9% of CdS, respectively. The quasi-Fermi level of electrons of -0.42 V (NHE) is not significantly changed. These alumina grafted semiconductor photocatalysts enable the linear addition of cyclopentene, cyclohexene, and α-pinene to N-adamantylimines affording novel homoallyladamantylamines in isolated yields of 21-85% through a regioselective C-C heterocoupling of intermediate allyl and α-aminobenzyl radicals. As by-products hydrodimers of the imine are formed by C-C homocoupling of the benzylic radicals. Different from heterocoupling, the homocoupling is a stereospecific process directed by the nature of the olefin employed in the reaction.
authors.affiliation: Department of Chemistry and Pharmacy Universität Erlangen-Nürnberg, Egerlandstr. 1, D-91058 Erlangen, Germany.
authors.forename: Müge
authors.initials: M
authors.lastname: Aldemir
authors.forename: Frank W
authors.initials: FW
authors.lastname: Heinemann
authors.forename: Horst
authors.initials: H
authors.lastname: Kisch
mesh_terms: D000537:Aluminum Oxide / Q000737:chemistry*; D000547:Amantadine / Q000138:chemical synthesis / Q000737:chemistry*; D019187:Cadmium Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003516:Cycloparaffins / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008027:Light; D008968:Molecular Conformation; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*
chemical_list: D019187:Cadmium Compounds; D003516:Cycloparaffins; D007097:Imines; D013440:Sulfides; C034939:cadmium sulfide; D000547:Amantadine; D000537:Aluminum Oxide