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Structure and reactivity of α,β-unsaturated ethers—XIV: Protonation of cis- and trans-1-ethoxybuta-1,3-dienes

✍ Scribed by T. Okuyama; T. Sakagami; T. Fueno

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 377 KB
Volume: 29
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)83390-1

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✦ Synopsis

The acid-catalysed hydrolysis and alcohol addition of cis-and trans-1-ethoxybuta-1,3dienes have been investigated. It was found by product analyses with deuterium incorporation experiments that in both the reactions the cis isomer protonates at the 2-position as well as at the 4-position while the truns isomer protonates exclusively at the 4-position. The kinetic experiments showed that the tram isomer is much more reactive than the cis isomer. The possible origin of the observations is discussed.

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