Methyl undec-9-enoate

Bromofluorination of dodec-2-ene, styrene, and methyl undec-10-enoate are carried out using similar conditions but using l,3-dibromo-5,5-dimethylhydantoin instead of A-halosuc-cinimide however, chlorofluorination with A-chlorosuccinimide as a chlorinating reagent is not successful at all and starting alkenes are recovered unchanged.336... 

Two types of side reaction have been noted. The catalyst system WCVMe4Sn generates a certain amount of HCl, which adds to terminal double bonds to the extent of about 10% of the metathesis reaction (Baker 1977). The catalyst system WCl6/Et3B causes some double-bond shift in the substrate prior to metathesis with methyl undec-lO-enoate (10) a series of products of the type MeOCO (CH2)gCH=CH(CH2) COOMe are formed, the yield decreasing as n decreases from 8 (the direct metathesis product) to 7, 6, and 5 (Nakamura, R. 1976a). 

Hydrosilylation of methyl imdec-lO-enoate with various silanes has been carried out on a laboratory scale [Eq. (1)]. In a typical experiment 10.0 mmol of methyl undec-lO-enoateand 10.0 mmol ofthe silane were dissolved in 8 mL of cydohexane. 

The hydrosilylation of methyl undec-lO-enoate 1 or methyl linoleate 2 (Scheme 1) was carried out with different hydrosilanes using dried hexachloroplatinic acid as homogeneous catalyst. The results are given in Tables 1 and 2. 

Hydrosilylation of methyl undec-lO-enoate 1 or methyl linoleate 2 with different hydrosilanes. 

Table 1. Hydrosilylation of methyl undec-lO-enoate 1 with different hydrosilanes (conditions stoichiometric amount of hydrosilane, 1 mol% HaPtCI, 40 C, 2 h, solvent cyclohexane/propylene carbonate).

Oxo esters undergo an intramolecular dicarbonyl coupling reaction on treatment with a low-valent titanium reagent to form a ketone. This was used in the synthesis of (Z)-7,l0,10-trimethyl-bicyclo[7.2.0]undec-6-en-2-one (4) from ethyl ( )-6-methyl-7-(4,4-dimethyl-2-oxocyclobutyl)-hept-5-enoate,108 Interestingly, the configuration of the isolated C -C double bond in the isolated product is sensitive to the reaction conditions. 

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