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Tri-N-Butylgermane

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Application: Effects free-radical reductive addition of alkyl halides to olefins with AIBN.1,2 RCH2I + H2C=CHCN ---> RCH2CH2CH2CN
Reduces benzylic chlorides 70 X faster than silyl hydrides.3
Initiates radical cyclization of polyenes.4
Reference: 1. Hershberger, J. Tetrahedron Lett. 1986, 26, 6289.
2. Pike, P. et al. Tetrahedron 1988, 44, 6295.
3. Mayr, H. et al. Angew. Chem., Int. Ed. Engl. 1992, 31, 1046.
4. Spino, C. et al. J. Org. Chem. 1999, 64, 5292.

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