
TY  - JOUR
A1  - Leban, M 
A1  - Fresco, J 
A1  - Das, M 
A1  - Livingstone, SE 
T1  - Hydrolysis of Monothio-&#946;-diketones. II. Hydrolysis of three fluorinated Monothio-&#946;-diketones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1974
VL  - 27
IS  - 11
SP  - 2357
EP  - 2360
KW  - 
UR  - https://doi.org/10.1071/CH9742357 
N2  - The rapid decomposition of the fluorinated monothio-&#946;-diketones RC(SH)=CHCOCF3, 4-(3?-bromophenyl)-1,1,1-trifluoro-4-mercaptobut-3-en-2- one (R = m-BrC6H4), 4-(4?-bromophenyl)-1,1,1-trifluoro-4-mercaptobut-3- en-2-one (R = p-BrC6H4) and 1,1,1-trifluoro-4-mercaptopent-3-en-2-one(R = Me), in acid solution has been shown to occur by hydrolytic cleavage to yield the ketone RCOCH3, hydrogen sulphide and probably trifluoroacetic acid. The pseudo first-order rate constants for these compounds are (8.0±0.3)x 10-3, min-1, (6.0 ± 0.6) x 10-3 min-1 and 0.12±0.01 min-1, respectively. The greater vulnerability of 1,1,1- trifluoro-4-mercaptopent-3-en-2-one, compared to the other two monothio-&#946;-diketones, towards hydrolytic cleavage is related to the nature of the R substituent in that conjugation involving the terminal aromatic ring stabilizes the monothio-&#946;-diketone. 
ER  -

