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

Philippe Renaud | Zendy; Michèle Gerster | Zendy; Marco Ribezzo | Zendy

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

Author(s) -

Philippe Renaud,

Michèle Gerster,

Marco Ribezzo

Publication year - 1994

Publication title -

chimia international journal for chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.387

H-Index - 55

eISSN - 2673-2424

pISSN - 0009-4293

DOI - 10.2533/chimia.1994.366

Subject(s) - stannane , chemistry , radical , trimethylsilyl , substituent , medicinal chemistry , electrophile , nucleophile , reagent , photochemistry , organic chemistry , catalysis

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) relative to the H-atom and 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 transition state. The 1-substituted vinylsilanes which are produced by radical allylation with 2 have been converted by protiodesilylation and ozonolysis to alkenes and α-hydroxy ketones.

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