Through-Bond Interaction in the Trifluoroethanolysis of 4-Oxo-2eq-adamantyl Triflate and Its Essential Vanishing in the Corresponding 2-Phenyl Substituted Trifluoroacetate

Autor: Yoshida, Masayasu, Mitsuhashi, Koichi, Kimura, Tsutomu, Takeuchi, Ken’ichi, Fukuyo, Emiko, Yanagi, Kazunori
Zdroj: Chemistry Letters; September 1992, Vol. 21 Issue: 9 p1771-1774, 4p
Abstrakt: Attachment of an oxo substituent on the 4-position of 2-adamantyl triflate alters the rate of trifluoroethanolysis at 25 °C by respective factors of 10−1.1and 10−2.5for 2eq- and 2ax-triflates, and 10−2.9and 10−2.5for the corresponding 2-phenyl-2eq- and -2ax-adamantyl trifluoroacetates, indicating the presence of through-bond interaction in the secondary equatorial and its essential vanishing in the 2-phenyl system. Product distributions agree with this notion.
Databáze: Supplemental Index