5- Decene

Composition, weight percent Octene-1 trans-Octene-2 cis-Octene-2 mixed-0ctene8-3. tran 0.ctjrie 4 Nonene 1. OeteneJ Isoolefini  

Dutillation range, F 7nitial boiling j omt Orv point Specific gravity of liquid at 60/60 F 255.0 0.724 

Nonvolatile matter, grams/100 ml Flash point, approximate, F 0.0005 

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In contrast to oxidation in water, it has been found that 1-alkenes are directly oxidized with molecular oxygen in anhydrous, aprotic solvents, when a catalyst system of PdCl2(MeCN)2 and CuCl is used together with HMPA. In the absence of HMPA, no reaction takes place(100]. In the oxidation of 1-decene, the Oj uptake correlates with the amount of 2-decanone formed, and up to 0.5 mol of O2 is consumed for the production of 1 mol of the ketone. This result shows that both O atoms of molecular oxygen are incorporated into the product, and a bimetallic Pd(II) hydroperoxide coupled with a Cu salt is involved in oxidation of this type, and that the well known redox catalysis of PdXi and CuX is not always operalive[10 ]. The oxidation under anhydrous conditions is unique in terms of the regioselective formation of aldehyde 59 from X-allyl-A -methylbenzamide (58), whereas the use of aqueous DME results in the predominant formation of the methyl ketone 60. Similar results are obtained with allylic acetates and allylic carbonates[102]. The complete reversal of the regioselectivity in PdCli-catalyzed oxidation of alkenes is remarkable. 

Furthermore, treatment of the aminopalladation product with bromine affords aziridines[176]. The aziridine 160 was obtained stereoselectively from methylamine and 1-decene in 43% yield. The aminopalladation of PdCl2 complexes of ethylene, propylene, and 1-butene with diethylamine affords the unstable ir-alkylpalladium complex 161, which is converted into the stable chelated acylpalladium complex 162 by treatment with CO[177],... 

Acid catalyzed hydration converts alkenes to alcohols with regioselectivity according to Markovnikov s rule Frequently however one needs an alcohol having a structure that corresponds to hydration of an alkene with a regioselectivity opposite to that of Markovnikov s rule The conversion of 1 decene to 1 decanol is an example of such a transformation... 

There is a pronounced tendency for boron to become bonded to the less substituted car bon of the double bond Thus the hydrogen atoms of diborane add to C 2 of 1 decene and boron to C 1 This is believed to be mainly a steric effect but the regioselectivity of addition does correspond to Markovmkov s rule m the sense that hydrogen is the neg atively polarized atom m a B—H bond and boron the positively polarized one... 

One of the mam uses of the linear a olefins prepared by oligomerization of ethylene is in the preparation of linear low density polyethylene Linear low density polyethylene is a copoly mer produced when ethylene is polymerized in the presence of a linear a olefin such as 1 decene [H2C=CH(CH2)7CH3] 1 Decene replaces ethylene at random points in the growing polymer chain Can you deduce how the structure of linear low density polyethylene differs from a linear chain of CH2 units ... 

The a-methylene groups also add to double bonds eg, 1-decene at 160°C gives up to 80% of a-decylbutyrolactone (160). With photochemical initiation similar additions take place at room temperature (161). 

In cases where the alkene is soluble, up to 30 S of the aqueous DMF can be mixed with the alkene to facilitate controlled addition. With 1-decene, QHF forms a two-phase mixture. 

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