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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 16, Number 8
BKCSDE 16(8)
August 20, 1995 

Menschutkin-Type Reaction of Substituted Benzyl Arenesulfonates with Substituted N,N-Dimethylanilines
Sung Hong Kim, Soo-Dong Yoh, Mizue Fujio*, Hiroshi Imahori*, Masaaki Mishima*, Yuho Tsuno*
The substituent effects in the second-order reaction of Z-substituted benzyl tosylates and benzyl X-benzenesulfonates with Y-substituted N,N-dimethylanilines (DMAs) were studied in acetonitrile at 35 ℃. Rate constants for the reaction of Z-benzyl tosylates with DMAs exhibited a curved Hammett plots, and the apparent ρZ values increased negatively in the following sequence Y=m-NO2>H>p-MeO>p-NMe2. This means the weaker nucleophile magnifies the effect of the benzyl substituent Z. The plot of ρY against log (kZ/kH)Y=H showed good linear relation with a slope of 0.57 and it was discussed that the change in transition state structure was mainly attributed to C-N bond formation. The
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