2- Nonanone 2-Nonenal, 538,

Oxidation of 3-acetoxy-l-nonene (14) at 50 C gave a mixture of the methyl ketone (15) and 1-ace-toxy-3-nonanone (16) in 33% and 17% yields. The latter was formed by regioselective oxidation of 1-acetoxy-2-nonene, itself formed by the allylic rearrangement of (14) promoted by Pd ions (equation 11). 

Figure 4. Testosterone concentration (ng/ml) in temporal gland secretion and relative abundance of four groups (I-IV) of compounds present in TGS over the course of musth in Tunga, an Asian bull elephant (a different elephant from the previous figures). Group I cyclohexanone, benzoic acid, phenylacetic acid, phenylpropanoic acid, octanoic acid, 3-octen-2-one and4-n-nonylphenol. Group II 5-nonanol, 2-hydroxyacetophenone, 1,3 dihydro-2H-indol-2-one, 2-nonanone, unidentified and 3-nonen-2-one. Group III phenol, decanoic acid and famesol. Group IV 4-hexenoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid and dotriacontanol.

Nonanal 1,3-Nonanediol acetate, mixed esters Nonanoic acid 2-Nonanol 2-Nonanone 3-Nonanon-1-yl acetate trans-2-Nonenal cis-6-Nonen-1-ol trans-2-Nonen-1-ol n-Nonyl acetate... 

Cyclohexylpropanol Diisobutyl ketone Isononyl aldehyde 2-Methyloctanal Nonanal 2-Nonanone cls-6-Nonen-1-ol trans-2-Nonen-1-ol Trimethylcyclohexanol C9H18O2 Amyl butyrate Amyl isobutyrate n-Butyl isovalerate N-Butyl-2-methylbutyrate Butyl valerate Ethyl heptanoate Heptyl acetate... 

Hydroxy-l-nonene allowed to react with activated MnOg in benzene in the presence of diethylamine -> l-diethylamino-3-nonanone. Y 78%. Also with hemiketal formation s. G. Saucy and R. Borer, Helv. 54, 2121 (1971). 

Bridged bicyclo[3.2.1]octenes and bicyclo[3.3.1]nonenes are obtained when this reaction is carried out in an intramolecular mode. The nucleophiles are generated in appropriately functionalized side chains at C5 of the tricarbonyl( n -cyclohexadiene)iron complexes. Acyclic (Ti -l,3-butadiene)Fe(CO)3 complexes with fimctionalized side chains at the terminal position of the diene ligands provide fused bicyclo[3.3.0]octanones and bicyclo[4.3.0]nonanones (Scheme 4-121). Up to four new stereogenic centers are established in a controlled way in the course of this reaction. ... 

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