Birch reduction styrene

Intramolecular protonation on the more hindered face of a steroid from a neighbouring hydroxyl group best explains a reversal of diastereoselectivity in the Birch reduction of styrene double bonds.266 The kinetics and product distribution of lithium metal reduction of benzaldehyde to benzyl alcohol in THF have been studied electron transfer from Li to PhCHO occurs in a slow step, but absorption of the PhCHO onto the metal surface is also crucial in determining the overall kinetics. The proposed mechanism successfully accounts for the formation of minor products, benzoin and... 

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