TY - JOUR
T1 - New approaches to sugar-functionalised 2,2':6',2"-terpyridines based upon tetrafluorophenoxy spacers: crystal and molecular structures of 4'-(tetrafluoro-4-hydroxyphenyl)-2,2':6',2"-terpyridine and 4'-(4-methoxytetrafluorophenyl)-2,2':6',2"-terpyridine
AU - Constable, Edwin
AU - Kariuki, Benson
AU - Mahmood, Azad
PY - 2003/3/1
Y1 - 2003/3/1
N2 - The new ligand 4'-pentafluorophenyl-2,2':6',2"-terpyridine (2) has been prepared with a view to utilising the electrophilic reactivity at the 4-position of the substituent to provide access to sugar-functionalised compounds. Although 2 reacts cleanly with simple alcohols, attempts to incorporate spacers or to attach sugars were unsuccessful. However, dealkylation of the 4'-(4-alkoxytetrafluorophenyl)-2,2':6',2"-terpyridines gave the corresponding phenol in good yield. Solid state structures of 4'(tetrafluoro-4-hydroxyphenyl)-2,2':6',2"-terpyridine (5) and 4'-(4-ethoxytetrafluorophenyl)-2,2':6',2"-terpyridine (4) are reported; the former compound has an extremely unusual cis, trans configuration of the pyridine rings as a result of intermolecular hydrogen bonding involving the phenol. Iron(II) complexes of 2 and 4 have been prepared; the compounds behave as typical tpy ligands and the fluorinated phenyl substituents are strongly electron-withdrawing. The reaction of the phenol 5 with electrophiles allows access to new 4'-(4-alkoxytetrafluorophenyl)-2,2':6',2"-terpyridines and by using 2-bromoethyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside as electrophile, the, glucose-functionalised ligand 9 and the iron(II) complex [Fe(9)(2)][PF6](2) were prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.
AB - The new ligand 4'-pentafluorophenyl-2,2':6',2"-terpyridine (2) has been prepared with a view to utilising the electrophilic reactivity at the 4-position of the substituent to provide access to sugar-functionalised compounds. Although 2 reacts cleanly with simple alcohols, attempts to incorporate spacers or to attach sugars were unsuccessful. However, dealkylation of the 4'-(4-alkoxytetrafluorophenyl)-2,2':6',2"-terpyridines gave the corresponding phenol in good yield. Solid state structures of 4'(tetrafluoro-4-hydroxyphenyl)-2,2':6',2"-terpyridine (5) and 4'-(4-ethoxytetrafluorophenyl)-2,2':6',2"-terpyridine (4) are reported; the former compound has an extremely unusual cis, trans configuration of the pyridine rings as a result of intermolecular hydrogen bonding involving the phenol. Iron(II) complexes of 2 and 4 have been prepared; the compounds behave as typical tpy ligands and the fluorinated phenyl substituents are strongly electron-withdrawing. The reaction of the phenol 5 with electrophiles allows access to new 4'-(4-alkoxytetrafluorophenyl)-2,2':6',2"-terpyridines and by using 2-bromoethyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside as electrophile, the, glucose-functionalised ligand 9 and the iron(II) complex [Fe(9)(2)][PF6](2) were prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.
UR - http://www.scopus.com/inward/record.url?scp=0037340378&partnerID=8YFLogxK
U2 - 10.1016/S0277-5387(02)01400-6
DO - 10.1016/S0277-5387(02)01400-6
M3 - Article
VL - 22
SP - 687
EP - 698
JO - Polyhedron
JF - Polyhedron
IS - 5
ER -