Upon metalation and subsequent electrophilic trapping, 2-fluoronaphthalene inevitably gives rise to regioisomeric mixtures in varying proportions, whereas 2-(trifluoromethyl) naphthalene undergoes deprotonation either at the 1- or the 3-position, depending on the choice of the reagent. On the other hand, 2-(trifluoromethoxy) naphthalene and 2-methoxynaphthalene react exclusively at the 3-position when, respectively, sec-butyllithium and superbasic reagents are employed. Steric repulsion by the peri hydrogen in combination with crowding due to coordination of the lithium atom with the methoxy group disfavors attack at the 1-position.
Type
research article
Web of Science ID
WOS:000276909600019
Authors
Publication date
2010
Published in
Issue
9
Start page
1531
End page
1535
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
December 16, 2011
Use this identifier to reference this record