- 作者: Michel Holler, Alain Burger and Jean-Francois Biellmann
- 中文摘要: Thioether 4-[(1'E,3'E)-4'-phenylsulfanyl-l',3'-butadienyl]pyridine 8 and sulfone 4-(4'-phenylsulfonyl-l',3'-butadienyl)pyridine 14 were prepared by reaction of the carbanions derived from allylic thioether or allylic sulfone with isonicotinaldehyde. The reaction with the sulfonyl carbanion occurred at the a position and on heating the alcolate gave the dienic sulfone 14. The corresponding pyridinium iodide 10 and 15 were prepared by reaction with methyl iodide, respectively, on pyridine derivates 8 and 14. The dienic pyridinium thioether 10 showed a long wavelength absorption band centered at 420 nm. The reaction of dienic pyridinium sulfone 15 with thiophenol gave the dienic pyridinium thioether 10 by a nucleophilic vinylic substitution. The reaction of sulfone 15 with glutathione was of second order and the rate constant was 8.5 M-1s-1 at 30 ?/fontC and Ph 7, about 500 times smaller than the rate constant observed with (E)-1-methyl-4-(2-methylsulfonyl-l-ethenyl)pyridinium iodide 1. The dienic pyridinium thioether 10 was a negative solvatochrome.
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