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In this transformation, initial electrophilic ¦Ð -complexation of a carbon¨Ccarbon double bond leads to electron deficiency at the carbon site which is vicinal to the C Sn bond. Stabilization of the developing ¦Â -carbocation occurs with alignment of the C Sn single bond, and orbital overlap provides a description of a non-classical cation in which the stannyl substituent carries a substantial fraction of the positive charge. Formation of a carbon¨Ccarbon double bond proceeds with loss of the stannyl cation, and thus, electrophilic substitution of the tin substituent has taken place with allylic transposition. |
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