Abstract
The racemic title compound, [Fe(C5H5)(C16H27O2)], comprises an α,ω-diol-substituted undecyl chain with a ferrocenyl substituent at at one terminus. The alkane chain is inclined to the substituted ring of the ferrocene grouping by 84.22 (13)°. The ferrocene rings are almost eclipsed and parallel. The crystal structure features O-H⋯O and C-H⋯O hydrogen bonds and C-H⋯π contacts that stack the mol-ecules along the c-axis direction. A Hirshfeld surface analysis reveals that H⋯H inter-actions (83.2%) dominate the surface contacts.
Highlights
The title compound, 1, is a rare example of a ferrocene molecule substituted with an extended, in this instance 11-membered, alkane chain
It was synthesized to provide a ferrocenyl-substituted diol for the preparation of polyesters with regular pendant electroactive groups
Friedel–Crafts methodology (Saji et al, 1991) provided the 1-ferrocenyl-undec-10-en-1-one precursor. This was reduced to the racemic alcohol 1-ferrocenyl-undec-10-en-1-ol (2) using LiAlH4
Summary
The title compound, 1, is a rare example of a ferrocene molecule substituted with an extended, in this instance 11-membered, alkane chain. Friedel–Crafts methodology (Saji et al, 1991) provided the 1-ferrocenyl-undec-10-en-1-one precursor. Hydroboration of ferrocenylalkenes has been previously reported (Lo Sterzo et al, 1984) using borane generated in situ from NaBH4/BF3ÁOEt2 This method was unsuitable as a means of preparing 1 from 2, the ferrocenylmethanol moiety being susceptible to attack by BF3, and the resultant loss of OHÀ abetted by the formation of the stable -ferrocenyl carbenium ion. This prediction was borne out by experiment, the Lewis acid attack resulting in synthesis of 1-ferrocenyl-undec-10-ene and 1-ferrocenyl-undec-11-ol.
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