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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 15, Number 9
BKCSDE 15(9)
September 20, 1994 

Acid-Promoted Ring Cleavage Reactions of Silacyclohex-3-ene Derivatives
Myong Euy Lee*, Jeong Hyun Kim, Chang Hwan Kim
The acid-promoted cleavage of the E-and Z-isomers of 1-phenyl-6-neopentyl-1,3,4-trimethyl-1-silacyclohe x-3-ene(Ⅱ) under various conditions gave clean and nearly quantitative formation of the ring-opened 2,3,7,7-tetramethyl-5-(X)silyl-1-octene products (X=OMe, Cl, OH). The possible mechanism for the formation of the ring-opened products was suggested that the initial protonation of Ⅱ at C-4 would give a carbocation oriented so that they are β to the silicon atom, and the subsequent nucleophilic attack at silicon would give rise to the observed products (Ⅵ, Ⅶ, Ⅷ).
729 - 732
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