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2004
Cyclopentane derivatives
Q 0030
Radical Carbonylation of 1,5-Enynes Using TTMSS as a Chain Carrier. UnexFormation of Persistent 3-Silyl-1-siloxyallyl Radicals Serving as a Chain
49- 066 pected
Breaking Path. — Radical carbonylation of 1,5-enynes (I) and (V) using silane (III)
as radical mediator affords the expected carbonylative cyclization products (IV) and
(VI), resp., in poor yields. The isolation and characterization of reaction by-products
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 to the
O—C double bond of the initially formed cyclopentanones. — (FUKUYAMA, T.;
UENOYAMA, Y.; OGURI, S.; OTSUKA, N.; RYU*, I.; Chem. Lett. 33 (2004) 7,
854-855; Dep. Chem., Fac. Arts Sci., Osaka Prefect. Univ., Osaka 599, Japan; Eng.)
— M. Paetzel
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