Tributyl[2-(trimethylsilyl)-prop-2-enyl]stannane: A Highly Efficient Reagent for the Allylation of Radicals

Tributyl[2-(trimethylsilyl)-prop-2-enyl]stannane: A Highly Efficient Reagent for the Allylation of Radicals

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Allylation rates of radicals with tributyl[2-(trimethylsilyl)prop-2-enyl]stannane (2) have been compared with the ones of the (prop-2-enyl)stannane (3) and [2-(methyl)-prop-2-enyl]stannane (4).The Me3Si substituent showed a rate-accelerating effect (4.2:1 to 6.

5:1) relati ve to the H-atom and Wii the Me group for nucleophilic radicals.With electrophilic radicals, the Me group has a better rate accelerating effect than the Me3Si group.All these results can be understood by postulating a partially polarized ORG WALNUTS transition state.

The 1-substituted vinylsilanes which are produced by radical allylation with 2 have been converted by protiodesilylation and ozonolysis to alkenes and ?-hydroxy ketones.