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Please login to access the full content or check if you have access via20.8.4.1.1.3 Variation 3: Arylation of Thiocarboxylic Acids
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Collier, S. J., Science of Synthesis, (2007) 20, 1618.
S-Aryl thioesters 54 can be prepared in reasonable yields by treatment of sodium thioacetates or thiobenzoates with dry arenediazonium 1,2-benzenedisulfonimides 53 (Scheme 21).[175] S-Aryl thioesters can also be prepared from thiocarboxylates and arenediazonium tetrafluoroborates[176–178] or diaryliodonium salts.[179] With highly activated aryl halides, such as 1-chloro-2,4-dinitrobenzene, direct displacement of the halide with thiocarboxylate salts gives S-aryl thiocarboxylates in good yields.[180,181] With less-activated aryl halides, such as iodopentamethylbenzene, treatment with copper(I) thiocarboxylate salts[182] in hexamethylphosphoric triamide[183] gives the expected thiocarboxylic acid S-esters.
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References
[175] | Meeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeee, M., Meeeeeeee, (8888), 8888. |
[176] | Meeeeeee, M.; Meee, M.; Meeeeeeee, M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[177] | Meeeeeee, M.; Meee, M.; Meeeeeeee, M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[178] | Meeeeee, M.; Meee, M.; Meeeeeee, M.; Meee, M., Meee. Meee. Meee., (8888) 888, 888. |
[179] | Mee, M.-M.; Meee, M.-M., Meeeeeeee, (8888), 888. |
[180] | Mee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
[181] | Meeeeeee, M.; Meeee, M., Mee. Meeee. Meee. Meee. Mee., (8888) 88, 88; Meee. Meeee., (8888) 88, 888888. |
[182] | Meee, M. M.; Meee, M. M. M., Meeeee M. Meee., (8888) 8, 888. |
[183] | Meeee, M.; Meeeee, M.; Meeeeee, M.; Meeeee, M., Meeeeeeee, (8888), 88. |
[184] | Meee, M.; Meeee, M.; Meeeee, M., M. Meeeeeeeeee., M, (8888) 88, 8888. |
[185] | Meeeeee, M.; Meeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeeee, M., Meeeeeeee, (8888), 8888. |
[186] | Meeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeee, M.; Meeeeeeee, M., Meeeeeeee, (8888), 88. |
[187] | Meeeeee, M.; Meeeee, M.; Meeeeeeeeee, M.; Meeeeee, M.; Meeee, M.; Meeeeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
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- 8.Meeeee-Meee, (8888) M 8-8, 888.