cis-5-Mesyloxycyclooctlytrimethylstannane solvolyses in 80% ethanol–20% water ca. 800 times faster than the trans-isomer and affords exclusively bicyclo[3.3.0]octane, consistent with a stereoelectronically regulated 1,5-percaudal interaction (ε-effect) from the C-Sn σ-bond.
B. H. Riches and W. Kitching, Chem. Commun., 1996, 1907 DOI: 10.1039/CC9960001907
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