
TY  - JOUR
A1  - Bolton, R 
A1  - Pilgrim, AJ 
T1  - Nucleophilic Displacement in Polyhalogenoaromatic Compounds. XV. The Azulene-6-yl Substituent
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1993
VL  - 46
IS  - 8
SP  - 1119
EP  - 1124
KW  - 
UR  - https://doi.org/10.1071/CH9931119 
N2  - 6-(p- Fluorophenyl )-4,8-dimethylazulene (1) undergoes methoxydefluorination ( NaOMe ; Me2SO/MeOH, 9:1, v/v; 323 K) at a rate 1100 times that of fluorobenzene under the same conditions. Substituents (1-NO2, 1,3-Cl2) showed effects similar to those in the benzene system. Both the electron-withdrawing effect of the azulen-6-yl substituent and the efficacy of transmission of substituent effects across the polyannular system are unusually large, and reflect the polarizable and dipolar nature of the azulene system. 
ER  -

