Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Acid-Promoted Ring Cleavage Reactions of Silacyclohex-3-ene Derivatives

  • Published : 1994.09.20
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Abstract

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 ${\beta}$ to the silicon atom, and the subsequent nucleophilic attack at silicon would give rise to the observed products (VI, VII, VIII).

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References

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  2. Hosomi–Sakurai reactions of silacyclohexenes vol.5, pp.17, 1994, https://doi.org/10.1039/b709318g