2 -Undecenal

Substituted TMM complexes also cycloadd to aldehydes in the presence of a tin cocatalyst such as MesSnOAc and MesSnOTs [31]. Reaction of 2-heptenal with methyl precursor (6) gave a mixture of methylenetetrahydrofurans (68) and (69). This regioselectivity is reversed with 10-undecenal and methyl precursor (5), where adduct (70) now predominates over (71). As in the carbocyclic system, the phenylthio group also functions as a regiocontrol element in reaction with cyclohexyl aldehyde. The initially formed adduct (72) eliminates the element of thio-phenol on attempted allyl rearrangement, and the overall process becomes a cycloaddition approach to furans (Scheme 2.21) [20]. 

Fatty Decanal Ethyl nonanoate Heptyl alcohol Lauryl alcohol, aldehyde Nonanal Octanal l-Octanol Undecanal 10-Undecenal. 

Aldehydes that contain isolated double bonds, such as 10-undecenal, citronellal, 3-cyclohexene-l-carboxaldehyde and norbornene carboxaldehyde. ... 

A crown ether (19-[(10-undecen-l-yl)oxy]-4R,14R-(-)4,14-diphenyl-3,6,9, 12,5-pentaoxa-21-azabicyclo[15.3.1]heneicosa-l(21),17,19-triene) was used in a plastic membrane as chiral selector for the design of EPMEs [21]. These electrodes can differentiate between S- and R-l-phenylethylammo-nium ions. The values of the slopes obtained when different plasticizers were used for EPMEs design were between 51.3 and 60.6 mV/decade of... 

Table 1 Effect of the catalyst on copolymerisation of ethene with 10-undecen-l-ol...

In addition to allylic alcohols, other unsaturated alcohols react with halides to give carbonyl compounds. Although the reaction was slow (three days), the reaction of 10-undecen-l-ol (50) with iodobenzene afforded the aldehyde 52 in a high yield. In this... 

PE graft copolymers were synthesized from PE-OH by Inoue et al. using ATRP techniques, adopting similar techniques as mentioned above [74]. PE-g-PMMA and Polyclhylcnc-gra/f-poly( -bulyl acrylate) (PE-g-PnBA) were prepared through the combination of metallocene-catalyzed ethylene/10-undecen-l-ol copolymerization and conversion of the copolymer into P E-g-Br, as a macroinitiator, for ATRP. Well-defined graft copolymers, PE-g-PMMA and PE-g-PnBA, were confirmed by analyses of the detached side chains. Resulting PE-g-PMMA worked well as a compatibilizer. 

Surface polymerization of 2-hydroxyethyl methacrylate (HEMA), which possessed a functional group, at the initiation sites on the molded sheet of the PP macroinitiator was performed by Matsuo et al. using the ATRP-mediated CuBr/PMDETA catalyst system [148]. The molded PP sheet (d = 1.0 mm) was prepared by a molding press from PP-Br, which was synthesized by bromina-tion of propylene/10-undecen-l-ol copolymer (PP-OH Mn = 15 500, [-OH] = 3.8 units/chain). The ATRP of HEMA was carried out on the molded PP-Br... 

Another interesting castor oil-derived platform chemical is 10-undecenal, which is at the same time a challenging substrate for olefin metathesis. For the SM of 10-undecenal, Dixneuf et al. modified C3 and C5 by insertion of SnCl2 into one Ru-Cl bond [48]. Modification of C3 led to a binuclear complex, which showed a conversion of 70% at a catalyst loading of 0.33 mol%. On the other hand, both the modified and unmodified C5 gave conversions over 70% with catalyst loadings of 1.25 mol%, but also led to formation of a high amount of by-products. 

---