Premium
Notizen. Sterisch gesteuerte Reaktionswege von substituierten 2‐Norbornyl‐Kationen
Author(s) -
Martínez Antonio García,
Fraile Amelia García,
García Juan Manuel Sánchez
Publication year - 1983
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19831160237
Subject(s) - 2 norbornyl cation , chemistry , norbornane , steric effects , trifluoromethanesulfonate , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Steric Control in the Reaction of Substituted 2‐Norbornyl Cations The reaction of camphenilone ( 1b ) with trifluoromethanesulfonic anhydride (Tf 2 O) yields 7,7‐dimethyl‐1, exo ‐2‐bis(trifluoromethylsulfonyloxy)norbornane ( 4b ) (60%). 6,6‐Dimethyl‐2‐norbornanone ( 1c ) affords under the same conditions 6,6‐dimethyl‐2‐norbornen‐2‐yl triflate ( 5c ) (70%). The reaction pathways of the intermediate 2‐(trifluoromethylsulfonyloxy)‐2‐norbornyl cations are mostly controlled by steric factors, the inductive effect playing no significant role.