Ferrocenyl amide

Chiral ferrocenyl Amide/Carbosi- Rh Asymmetric Not specified Not specified Ultrafiltration High ees (98%) 90, 91... 

Dendritic ferrocenyl amide-derived nanoparticles have been nsed as chemiresistor sensors for the detection of volatile organic componnds. 

Catalytic [3 + 2]-cycloaddition of the carbonyl and azomethine ylides 129 with olefins gives the five-membered heterocycles 130 (Scheme 45). Longmire et al. reported that the catalytic asymmetric [3 + 2]-cycloaddition of the azomethine ylides 131 with dimethyl maleate in the presence of AgOAc and a bis-ferrocenyl amide ligand 133 gave the pyrrolidine triesters 132 in excellent yields with very high enantiomeric excesses (Scheme 46).122 As described in section 8, the [3 + 2]-cycloaddition reaction of diazo compounds with olefins proceeds similarly through the formation of carbonyl ylides. 

The lithiation of ferrocenyl amides with n BuLi (-)-3 proceeds with high enantioselec-tivity providing after quenching with an electrophile useful new chiral ferrocene derivatives like 24 (Eq. 13). [20]... 

Organometallic receptors for neutral guest species were first reported in 1991 by Gokel and co-workers.NMR studies revealed that bis-ferrocenyl amide 101 complexes A,A,iV, iV -tetramethyl-l,3-propanediamine, 1,4-diazabi-cyclo[2.2.2]octane (DABCO), and 3-propyladenine in CDCI3 solution with Aa = 341, 604, and 1,270 respectively, whereas 102 complexes 4-aminopyridine in THF-d solution with = 3,200 Electrochemical sensing was not reported. 

Bell and Hall have incorporated an organometallic unit into a crown by using the ferrocenyl unit as part of the ring or as a third strand. The unit is incorporated either as the 1,1 -diformylferrocene or the corresponding acid. In the former case, the bis-imine is prepared and reduced to give the saturated crown (see structure 24). In the latter case, the acid is converted into its corresponding chloride and thence into the diamide by reaction with a diamine. Diborane reduction affords the saturated amino-crown. Structure 24 could be prepared by either of these methods but the dialdehyde approach was reported to be poor compared to the amide approach which afforded the product in ca. 60% yield . 

Hollis TK, Overman LE (1997) Cyclopalladated ferrocenyl amines as enantioselective catalysts for the rearrangement of allylic imidates to allylic amides. Tetrahedron Lett 38 8837-8840... 

In 3, the amino functional group is two methylene units removed from the ferrocene nucleus. It appears from the instantaneous and quantitative formation of h from 3 that this feature minimizes steric effects and also enables 3 to undergo the Schotten-Baumann reaction readily without the classical a-metallocenylcarbenium ion effects providing any constraints. The IR spectrum of showed the characteristic N-H stretch at 3320 cm" (s), the amide 1 (carbonyl) stretch at 1625 an - -(s), the amide II (N—H) stretch at 1540 cm (s), and the amide III band at 1310 cm 1(m). In addition, characteristic absorptions of the ferrocenyl group were evident at 1100 and 1000 cm l (indicating an unsubstituted cyclopentadienyl ring) and at 800 cm"l. 

Reynes, 0., Maillard, F., Moutet, J. C., Royal, G., Saint-Aman, E., Stanciu, G., Dutasta, J. P., Gosse, I., Mulatier, J. C., Complexation and electrochemical sensing of anions by amide-substituted ferrocenyl ligands. J. Organomet. Chem. 2001, 637, 356-363. 

Optically active imidazolines are generally obtained from enantiopure 1,2-diamines. For example, chiral ferro-cenylimidazolines are prepared from ferrocenyl carboxylic acid 1241 (Scheme 310). Amide 1242 is activated by 0-alkylation with Et30 BF4, generating iminium ether tetrafluoroborate salt 1243. The formation of the imidazoline ring in 1244 is accomplished by condensation of 1243 with the chiral diamine 1245 at room temperature without the need to isolate the intermediate imidate 1243 <20050L4137>. 

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