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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 5
BKCSDE 31(5)
May 20, 2010 

Rate and Product Studies with 2-Methyl-2-Chloroadamantane under Solvolytic Conditions
Young Hoon Lee, Mi Hye Seong, Eun Sung Lee, Yong Woo Lee, Hoshik Won, Jin Burm Kyong*, Dennis N Kevill
2-Methyl-2-chloroadamantane, Grunwald-Winstein equation, Activation volume
Reactions of 2-methyl-2-chloroadamantane (1) in a variety of pure and binary solvents have been studied at various temperatures and pressures up to 80 MPa. The sensitivity (m) to changes in solvent ionizing power of the Grunwald- Winstein equation, and the activation volume (ΔV) are calculated from the specific rates. An excellent linear relationship (R = 0.997) for 1, log (k/k0) = 0.80YCl + 0.11, and the activation volume, ΔV = -15.2 ~ -10.2 mL.mol-1 were observed. These values are similar to those for solvolyses of 1-adamantyl halides over the full range of solvents, suggesting that the unimolecular mechanism involving ion pairs is rate-determining. These observations are also compared with those previously reported for the corresponding 1-adamantyl derivatives and chloroformate esters.
1209 - 1214
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