1.
Org Lett
; 3(12): 1881-4, 2001 Jun 14.
Article
in English
| MEDLINE
| ID: mdl-11405735
ABSTRACT
[see reaction]. 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.