Radical carbonylation of 1,5-enynes using TTMSS as a chain carrier. Unexpected formation of persistent 3-silyl-1-siloxyallyl radicals serving as a chain breaking path

Takahide Fukuyama, Yoshitaka Uenoyama, Shinya Oguri, Noboru Otsuka, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The radical carbonylation of 1,5-enynes 1a and 1b using TTMSS as radical mediator gave the predicted carbonylative cyclization products 2a and 2b, respectively, in poor yields. The isolation and characterization of reaction byproducts by X-ray crystallographic analysis suggest that the poor chain propagation can be attributed to the formation of long-lived 3-silyl-1-siloxyallyl radicals, produced by the addition of a (TMS) 3Si radical onto the O-C double bond of the initially formed cyclopentanones.

Original languageEnglish
Pages (from-to)854-855
Number of pages2
JournalChemistry Letters
Volume33
Issue number7
DOIs
StatePublished - 5 Jul 2004

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