Journal of the American Chemical Society p. 5957 - 5961 (1993)
Update date:2022-08-28
Topics:
Kupczyk-Subotkowska, Lidia
Saunders Jr., William H.
Shine, Henry J.
Subotkowski, Witold
Kinetic isotope effects (KIE) in the rearrangement of allyl vinyl ether (1, 3-oxa-1,5-hexadiene) to 4-pentenal (2) were measured for labeling with 14C at the 2-, 4-, and 6-positions and with 18O at the 3-position. BEBOVIB modeling calculations were applied successfully to the heavy-atom KIE and previously reported KIE for deuterium substitution at positions 4 and 6. From the calculations, it is deduced that the C4-O bond is 50-70% broken and the C1-C6 bond 10-30% formed in the transition structure. Further, there is strong coupling between the allyl and vinyloxy fragments, strong bonding within the allyl but relatively weak bonding within the vinyloxy fragment.
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