Base-catalyzed hydrogen isotope exchange of thiocamphor: α-thioenolization rate constants
Keyword(s):
The rates of base-catalyzed protium–deuterium exchange (α-thioenolization) of the exo and endo protons of thiocamphor (1), in 2:1 dioxane-D2O at 25.0 ± 0.5 °C, have been determined by monitoring the uptake of deuterium mass spectrometrically. The exo and endo exchange rate constants, 2.20 × 10−2 and 5.60 × 10−4 M−1 s−1, respectively, are 23.2 and 12.3 times larger than the rate constants for exo and endo exchange in camphor (2). Factors which may determine the rate enhancements are discussed.
2010 ◽
Vol 53
(11-12)
◽
pp. 704-715
◽
1971 ◽
Vol 93
(20)
◽
pp. 5088-5096
◽
1969 ◽
Vol 33
(1)
◽
pp. 49-64
◽
1993 ◽
Vol 25
(5)
◽
pp. 363-374
Keyword(s):
Keyword(s):