TY - JOUR

T1 - Synthesis and structures of some di- and triferrocenylmethane derivatives

AU - Garabatos-Perera, Jose Ramon

AU - Wartchow, Rudolf

AU - Butenschön, Holger

N1 - Funding information: We thank Octel Deutschland GmbH, Herne (Germany) and the Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr (Germany) for donations of ferrocene. This work was kindly supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, and the joint research initiative “Biologisch aktive Naturstoffe – Synthetische Diversität”.

PY - 2004/11/1

Y1 - 2004/11/1

N2 - Some triferrocenylmethane derivatives were prepared by reaction of triferrocenylmethanol (5) with triphenylcarbenium tetrafluoroborate followed by a nucleophile. Crystal structure analyses of triferrocenylmethane (7) and of 1,1,1-triferrocenyl-2,2-dimethylpropane (11) show that the conformation adopted by the triferrocenylmethyl group differs significantly with the steric bulk of the substituent at the central carbon atom. Treatment of 1,1′-bis(tributylstannyl) ferrocene (13) with 1 equiv. of butyllithium followed by chloroethylformiate affords complexes with one (14), two (15) or three ferrocenyl units (16) depending on the amount of chloroethylformiate used. Compound 16 is the first triferrocenylmethane derivative with substituents at the opposite cyclopentadienyl ring. Threefold lithiation of this compound is shown to work using butyllithium followed by dimethylformamide.

AB - Some triferrocenylmethane derivatives were prepared by reaction of triferrocenylmethanol (5) with triphenylcarbenium tetrafluoroborate followed by a nucleophile. Crystal structure analyses of triferrocenylmethane (7) and of 1,1,1-triferrocenyl-2,2-dimethylpropane (11) show that the conformation adopted by the triferrocenylmethyl group differs significantly with the steric bulk of the substituent at the central carbon atom. Treatment of 1,1′-bis(tributylstannyl) ferrocene (13) with 1 equiv. of butyllithium followed by chloroethylformiate affords complexes with one (14), two (15) or three ferrocenyl units (16) depending on the amount of chloroethylformiate used. Compound 16 is the first triferrocenylmethane derivative with substituents at the opposite cyclopentadienyl ring. Threefold lithiation of this compound is shown to work using butyllithium followed by dimethylformamide.

KW - Crystal structure analysis

KW - Ferrocene

KW - Lithiation

KW - Triferrocenylmethane

UR - http://www.scopus.com/inward/record.url?scp=5044252141&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2004.07.059

DO - 10.1016/j.jorganchem.2004.07.059

M3 - Article

AN - SCOPUS:5044252141

VL - 689

SP - 3541

EP - 3549

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 22

ER -