Photochemistry of acetylenic compounds 13. Kinetics and orientation of addition of 1-hexyne to six-membered cyclicα, β-enones

Autor: Serebryakov, É. P., Margaryan, A. Kh., Kucherov, V. F.
Zdroj: Russian Chemical Bulletin; February 1978, Vol. 27 Issue: 2 p359-363, 5p
Abstrakt: 1.Photocycloaddition of 1-hexyne to six-membered cyclica, ß-enones involves electrophilic attack of the triplet-state enone on the triple bond; the reaction is characterized by a constant? of 1.554, which excludes a concerted mechanism.2.The increased enone ring size reduces the rate of reaction in comparison with 2-cyclopentenone.3.We cannot unequivocally attribute the orientation of the reaction to any one electronic or steric effect of the enone substituent.
Databáze: Supplemental Index