Abstract
(formula presented) Oxyanion substitution of enyne-allenes causes both Myers-Saito and Schmittel cyclizations to switch their product formation preferences from diradicals to polar, closed-shell singlets. The oxyanion stabilization is larger for the Schmittel products than the Myers-Saito products because the latter must sacrifice aromaticity to maximize interaction. The changing character of the different reaction paths is reflected in their activation energies.
Original language | English (US) |
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Pages (from-to) | 1881-1883 |
Number of pages | 3 |
Journal | Organic Letters |
Volume | 3 |
Issue number | 12 |
DOIs | |
State | Published - Jun 14 2001 |