The stereochemistry of the transition state in the CLAISEN rearrangement of crotyl propenyl ethers (2) has been established. By heating trans, cis‐, cis, cis‐ and trans, trans‐crotyl propenyl ether at 142,5°, erythro and threo 2, 3‐dimethylpent‐4‐en‐1‐al (3 and 4) were obtained. From the ratio 3/4 it was shown that the rearrangement of the three ethers largely involves (97–98%) a chair‐like transition state.
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Vittorelli et al. (1968) studied this question.
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