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5.2.29.7.2 Variation 2: Tin–Lithium Exchange

DOI: 10.1055/sos-SD-005-00593

Young, D.Science of Synthesis, (20035616.

Alkylstannanes bearing an α-alkoxy group undergo tinlithium exchange to provide a synthetically useful nucleophile. The intermediate α-alkoxystannane can be regarded as a masked carbinyl carbanion, reversing the usual electron density of the carbonyl functional group.[‌8‌] Without the stabilizing influence of the α-oxygen, the position of the equilibrium is determined by the thermodynamic stability of the alkyllithium species produced.[‌26‌] So the equilibrium depicted in Scheme 15 lies very much to the right, reflecting the thermodynamic stability of methyllithium over butyllithium.

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