Alkoxybenzyl allyl ethers

Rearrangement. Zeolite P has been used to induce rearrangement of alkoxybenzyl allyl ethers to aldehydes and ketones at room temperature (10 examples, 41-83%). 

The rearrangement reaction of a variety of alkyl phenyl ethers over a dealumi-nated HY zeolite has been shown to involve both intramolecular and intermolecular processes to afford phenol, (alkoxyalkyl)benzenes and alkylphenols as the main products. o-Benzylphenol has been obtained as the exclusive product in the rearrangement of benzyl phenyl ether in the presence of montmorillonite. The mechanism for a novel zeolite /3-catalysed rearrangement of alkoxybenzyl allyl ethers to aldehydes and ketones has been investigated by the use of cross-over reactions and deuterium labelling. The reaction was found to be mainly intramolecular and has been described as a nucleophilic attack of the double bond on the electrophilic benzylic carbon of the ether-Lewis acid complex, followed by a... 

---