Super-electron donors : bis-pyridinylidene formation by base treatment of pyridinium salts

Murphy, J.A. and Garnier, J. and Park, S.R. and Schoenebeck, F. and Zhou, S.Z. and Turner, A.T. (2008) Super-electron donors : bis-pyridinylidene formation by base treatment of pyridinium salts. Organic Letters, 10 (6). pp. 1227-1230. ISSN 1523-7060 (https://doi.org/10.1021/ol800134g)

Abstract

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.

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  Item type:	Article
  ID code:	19761
  Dates:	Date Event 20 March 2008 Published
  Keywords:	super-electron donors, bis-pyridinylidene, pyridinium salts, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Strathprints Administrator
  Date deposited:	02 Jun 2010 17:02
  Last modified:	01 Dec 2022 01:39
  URI:	https://strathprints.strath.ac.uk/id/eprint/19761