Halocyclohexenylmethyl

An unusual [1,3]-rearrangement of aryl 2-halocyclohexenylmethyl ethers promoted by trifluoroacetic acid has been observed. Products due to a Claisen rearrangement were not formed and the proposed pathway for the process is outlined in Scheme 7. It has been shown that AICI3-mediated decomposition of A-phenoxybenzamide... 

An unusual [1,3]-rearrangement of aryl 2-halocyclohexenylmethyl ethers 161 was promoted by trifluoroacetic acid (since the thermal rearrangement failed because the ethers 161 are stable up to 240 °C). When the ethers 161 were exposed to TEA at room temperature, an extremely facile reaction afforded the products 162 in good yields (65-80%). However, no products of Claisen rearrangement were formed (equation 72). ... 

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