Super-electron donors: bis-pyridinylidene formation by base treatment of pyridinium salts.
Deprotonation of bispyridinium salt 7b affords bispyridinylidene 10, a very powerful neutral organic two-electron donor [E1/2 (DMF)=-1.13 V vs Ag/AgCl/KCl (sat)], presumably via the pyridinylidene 8. Donor 10 reduces aryl iodides and bromides to aryl anions in excellent yield and also reductively cleaves selected phenylalkylsulfones very efficiently.
Murphy
John A
JA
WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom. John.Murphy@strath.ac.uk
Garnier
Jean
J
Park
Stuart R
SR
Schoenebeck
Franziska
F
Zhou
Sheng-ze
SZ
Turner
Andrew T
AT
D004563:Electrochemistry; D004583:Electrons; D009682:Magnetic Resonance Spectroscopy; D011726:Pyridinium Compounds / Q000737:chemistry*
D011726:Pyridinium Compounds