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Young, D., Science of Synthesis, (2003) 5, 616.
Alkylstannanes bearing an α-alkoxy group undergo tin–lithium 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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References
[8] | Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[26] | Meeeee, M. M.; Meeeeeee, M.; Meeeeeeee, M. M.; MeMeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 888. |
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- 8.Meeeee-Meee, (8888) 88/8, 888.