Abstract
Abstract 1,1′-(1-Ferrocenyl-1,3,3-trimethylpropane-1,3-diyl)ferrocene and 1,2-(1-ferrocenyl-1,3,3-trimethylpropane-1,3-diyl)ferrocene are formed as cyclodimeric products during the synthesis of β-ferrocenyl carbinols, in relative ratios which depend on the reaction conditions. Their ratios and stabilities are examined, and calculated at the BP86 level of theory and several different isomers of the homoannular product were examined by DFT calculations. Keywords : Ferrocene, cyclodimeric products, carbinols, DFT calculation Introduction Ferrocenyl alcohols are very useful synthetic intermediates in the synthesis of many biologically active compounds, industrially important compounds, as ligands in homogenous catalysis, in material science ( e.g . in nonlinear optics) and in bio-organometallic chemistry as redox-active probes or candidates for drugs. 1,2 In a previous paper 3 we studied the nucleophilic substitution of diethyl malonate with ω-ferrocenylalkanols, derived carbinyl acetates, bromides and quaternary salts to α-ferrocenylalkylmalonates. These substrates can easily be reduced into the prochiral 2-(ω-ferrocenylalkyl)propane-1,3-diols. Furthermore, we examined the enzymatic esterification of these prochiral diols in order to determine a degree of desymmetrization depending on the length of the side chain,
Highlights
Ferrocenyl alcohols are very useful synthetic intermediates in the synthesis of many biologically active compounds, industrially important compounds, as ligands in homogenous catalysis, in material science and in bio-organometallic chemistry as redox-active probes or candidates for drugs.[1,2] In a previous paper[3] we studied the nucleophilic substitution of diethyl malonate with ω-ferrocenylalkanols, derived carbinyl acetates, bromides and quaternary salts to α-ferrocenylalkylmalonates
We examined the enzymatic esterification of these prochiral diols in order to determine a degree of desymmetrization depending on the length of the side chain, i.e., the distance between the ferrocene moiety and stereogenic center.[4]
It was shown earlier that secondary ferrocenyl carbinols can be dehydrated to give the corresponding vinyl-ferrocenes which under mild conditions undergo dimerization resulting in linear olefinic products
Summary
Experimental and DFT study of 2-ferrocenylpropan-2-ol cyclodimerization products. Abstract 1,1′-(1-Ferrocenyl-1,3,3-trimethylpropane-1,3-diyl)ferrocene and 1,2-(1-ferrocenyl-1,3,3trimethylpropane-1,3-diyl)ferrocene are formed as cyclodimeric products during the synthesis of β-ferrocenyl carbinols, in relative ratios which depend on the reaction conditions. Their ratios and stabilities are examined, and calculated at the BP86 level of theory and several different isomers of the homoannular product were examined by DFT calculations
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