T. Hattori, Mikio Suzuki, N. Tomita
1997
Citations
0
Influential Citations
14
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
1-Methoxynaphthalenes 3–7 having sulfonyl substituents SO2R (R = Me, Pri, But, OPh and N[CH2]3CH2) at the 2-position undergo displacement of the 1-methoxy group on treatment with the Grignard reagents 8a–d by a chelation-assisted conjugate addition–elimination process. Activating ability of these sulfonyl groups for the apparent nucleophilic aromatic substitution is compared with that of an ester group, isopropoxycarbonyl, and a sulfinyl group, tert-butylsulfinyl, and found to fall roughly in the order CO2Pri > SO2OPh > SO2N[CH2]3C H2 SO2 Alkyl SOBut . The activation order is interpreted as being the outcome of a balance between the electron-withdrawing strength of the 2-substituents and the steric hindrance caused by the Grignard reagents 8a–d on approach to the substrates 1-methoxynaphthalenes 1–7. Asymmetric binaphthyl coupling by reaction of the chiral sulfamoyl-substituted naphthalene 20 with 1-naphthyl Grignard reagents 8d,e is also reported.