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Stereoselective conversion of tetraalkyltin compounds to alcohols

✍ Scribed by James W. Herndon; Chao Wu


Book ID
104240317
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
251 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis


A stereoselective method for the conversion of a tributyltin group at an unactivated carbon atom has been achieved.

Reaction with bromine leads to preferential cleavage of a butyl group, giving an alkylbromodibutylstannane. Subsequent reaction with basic peroxide leads to preferential cleavage of the more-substituted carbon-tin bond and formation of the corresponding alcohol with retention of configuration.

Organotin reagents have emerged as valuable reagents for synthetic organic chemistry'.


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