"Nucleophilic substitution at an allylic substrate under SN2 conditions may proceed via nucleophilic attack at the y-carbon, especially when substitution at the a-carbon sterically impedes the normal SN2 reaction. These SN2' reactions with cyclohexenyl systems generally proceed via an anti addition of the nucleophile to the double bond, as depicted below (best overlap of participating orbitals)."
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George S. Zweifel and Michael Nantz, Modern Organic Synthesis (2006), Ch. 2. Stereochemical Considerations in Planning Syntheses
https://en.wikiquote.org/wiki/Nucleophilic_substitution
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Nucleophilic substitution
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