Preparation, spectroscopic characterization and crystal structures of ferrocenylalkanediols and derived acetates

( meso, dl)-3-(Ferrocenylmethyl)pentane-2,4-diol ( 3) was synthesized by reduction of 3-(ferrocenylmethyl)pentane-2,4-dione ( 2) with LiAlH 4 in a good yield and corresponding monoacetate 4 and diacetate 5 were prepared. Newly prepared compounds are characterized by elemental analysis, IR and NMR sp...

Full description

Saved in:
Bibliographic Details
Published in:Journal of molecular structure 2011-01, Vol.985 (2), p.413-418
Main Authors: Lapić, Jasmina, Bilić, Josipa, Cetina, Mario, Djaković, Senka, Rapić, Vladimir
Format: Article
Language:English
Subjects:
acetates
Crystal structure
dl-diol
Ferrocenylalkanediols and acetates
hydrogen bonding
meso
nuclear magnetic resonance spectroscopy
Self-assembly
X-ray diffraction
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:( meso, dl)-3-(Ferrocenylmethyl)pentane-2,4-diol ( 3) was synthesized by reduction of 3-(ferrocenylmethyl)pentane-2,4-dione ( 2) with LiAlH 4 in a good yield and corresponding monoacetate 4 and diacetate 5 were prepared. Newly prepared compounds are characterized by elemental analysis, IR and NMR spectroscopy and will be used as a substrate or standards for lipase mediated desymmetrization. The structures of 3-(ferrocenylmethyl)pentane-2,4-diol ( 3) and 2-(ferrocenylmethyl)propane-1,3-diol diacetate ( 8), which is derived from prochiral 2-(ferrocenylmethyl)propane-1,2-diol ( 6), were determined by X-ray crystal structure analysis. The conformation of the cyclopentadienyl rings is eclipsed in 3 and almost halfway between eclipsed and staggered in 8. One O−H⋯O hydrogen bond links the molecules of diol 3 into chains, while one weak C−H⋯π interaction self-assembles the molecules of diacetate 8 into dimers.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2010.11.040