Allylsilanes to Allylamines

Allylsilanes react with benzenetellurinyl trifluoroacetate in 1,2-dichloroethane to give allyl phenyl tellurium oxides. Addition of amines to the reaction mixtures results in the formation of allylamines  

The allyltrimethylsilane allylamine transformation is characterized by high regioselecti-vity. With arylamines, both cis- and tro 5-allylsilanes form tra 5-allylaraines. With sterically undemanding alkylamines 3-aminoalk-l-enes are formed with sterically demanding alkyl-amines mixtures of 3-aminoalk-1-enes and l-aminoalk-2-enes, and with bulky alkylamines only 1-aminoalk-2-enes are formed.  

Treatment of 2-methoxycyclohexyl phenyl tellurium oxide, prepared from cyclohexene and phenyl tellurium tribromide in methanol followed by hydrolysis of the tellurium dibromide, with 3-chloroperoxybenzoic acid in methanol caused ring contraction with formation of the dimethyl acetal of cydopentanecarbaldehyde .  

The dimethyl acetal of cyclohexanecarbaldehyde was similarly prepared from cycloheptene  

Irgolic Organo Tellurium Compounds with 2 Te —C Bonds or 1 Te = C Bond 

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This tellurium-mediated transformation of allylsilanes to allylamines proceeds with high regioselectivity3. 

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