Pentamethylcyelopentadienide in organic synthesis:nucleophilic addition of lithium pentamethylcyelopentadienide to aromatic aldehydes and carbon-carbon bond cleavage of the adducts affording the parent aldehydes

摘要

Treatment of aromatic aldehyde with lithium pentamethylcyelopentadienide provided the corresponding carbinol in excellent yield.The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene upon exposure to an acid or due to heating.The combination of the two reactions can represent a protection of aromatic aldehyde.