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Collier, S. J., Science of Synthesis, (2007) 20, 1634.
Thiocarboxylic acid S-esters can be prepared by a number of rearrangement reactions, ranging in complexity from simple to moderately complex. Simple reactions include the thermal isomerization of thiocarboxylic acid O-esters (e.g., 78) to give the thermodynamically more stable thiocarboxylic acid S-esters (e.g., 79); (Scheme 31).[326–330] Other rearrangement reactions include the base-mediated rearrangement of pyran-2-thiones to thiopyran-2-ones by a hydrolysis–conjugate addition–dehydration sequence,[331–333] and the photolytic rearrangement of 4-hydroxyphenacyl sulfides to S-alkyl (4-hydroxyphenyl)ethanethioates, although yields in this reaction are often low.[131]
Meeeee 88 Meeeeee Meeeeeeeeeeee ee e Meeeeeeeeeeeee Meee M-Meeee ee e Meeeeeeeeeeeee Meee M-Meeee[888]
Meeeeeee eeeeeeeeeeeee ee β-eee eeeeeeeeee 88 eeeee eee eeeeeeeeeeeee M-8-eeeeeeeeeeeeeeeeeeeeeee 88 ee eeeeeeeeee eeeeee eee eeeee eeee eee eeeeeeeeeeeee α-eeeeeee eeeeeeeeee eeeee eeee eeeeeeeeee (Meeeee 88).[888,888] Meeeeeeee, 8-eeeeeeeeeee 8-eeeeeeee-β-eeeeeee eeee α-eeeee eeee eeeeeeeeeeeeee eeee M-eeeeee ee eee Meeeeeee eeeeeeee,[888] eee α-eeeeee-α-(eeeeeeeeeeeee) eeeeeeeeee eeeeeeeee ee 8°M ee eeee eeeeeeeeee ee eeeeeeee eeeeee.[888]
Meeeee 88 Meeeeeeeeeeeee Meee M-Meeeee ee eee Meeeeeee Meeeeeeeeeeee[888]
Meeeeeeeee eeeeee 88 eee eeeeeee eee-eeeeee eeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeee 88 ee e eee-eeee eeeeeeee eeeeeeeee eeeeeeeee eeee eeeeeeeee eeeeeeeeeeee eeeeee eeeeeeeee 88 ee eeee ee α-eeeeee α-eeeeeeee eeeeee 88, eeeeeeee ee eeeeeeeee eeee eeeeee eeee eee e eeeee (Meeeee 88).[888] Meeeeeee ee eeeeeeeeeeee eee eeeeeee eeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeeee ee eee ee eeeeeeee eeeeee eeeee eeeeee eeeeeee ee eeeeeeeeeeeee eeeeeeeeee.[888] Meee eeeeeeeeee eee eeee eeeeee ee eeeee eeeeeeeee. Meee eeeeeeee eeeeeee eeee α-eeeee eeeeeeeeeeeeeeee eeeee, eee eeeeee eeeeeeeee ee α-eeeeee eee ee eeeeeeeeee ee e eeeeee ee eeeeeeee eeeeeee ee eee eeeeeee. Meeeeee ee eee eeeee eeeee eeeeeee ee eeeee eeeeeeeeeeee ee eee eeeeeee, ee eeee eee eeeeeeeee eeeeeeeeeeeeee eeee M-eeeee ee eeee eeeeeee.[888]
Meeeee 88 Meeeeeeeee ee Meeeeeeeee Meeeee eeee Meeeeeeeeee Meeeeeeeeeeeee Meee M-Meeeee[888]
M eeeee ee γ-eeeeee-eeeeeeeeeee eeeeeeeee eeeeeeee 88 (ee eeeee eeeeee) eeee α,β-eeeeeeeeeee eeeeeeeeeeeeee eeee M-eeeeee 88 ee e Meeee–Meeeeeee-eeee eeeeeeeeeeeee ee eeeeeeeee eeee eeeeeeeeeeeeee eeee eeeeeeeeeeeeee eeeee (MMMM) (Meeeee 88).[888] Mee eeeeeeee eee eeeeeee eeeeeeeeeeee ee eeeeeee eeeeeee ee eeeeee eeeeee ee β-eeeeeeeeeee; eeee ee e eeeeeeeeeee eeeeeee eeee eeeeeeee eeeeeeee.
Meeeee 88 Meeeeeeeeeeeee Meee M-Meeeee ee Meeee–Meeeeeee-Meee Meeeeeeeeeeeee[888]
M8 | M8 | Meeee (%) | Mee |
---|---|---|---|
Me | Me | 88 | [888] |
Me | (MM8)8Me | 88 | [888] |
Me | eMe | 88 | [888] |
Me | e-Me | 88 | [888] |
Me | (MM8)8Me | 88 | [888] |
e-Me | (MM8)8Me | 88 | [888] |
Mee | (MM8)8Me | 88 | [888] |
References
[131] | Meeeee, M.; Meeeeee, M.; Meee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[190] | eee eee Meeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeeee, M., Meee. Meee. Meee. Meee-Mee, (8888) 888, 88. |
[326] | Meeee, M.; Meee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
[327] | Meeee, M. M., Meeeeeeeeee Meee., (8888), 888. |
[328] | Meee, M.; Mee, M.; Meeee, M., Mee. M. Meeeee Meee., Meee M, (8888) 8, 88. |
[329] | Meeee, M.; Meee, M.; Mee, M., Meeeeeeeeee Meee., (8888), 8888. |
[330] | MeMeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[331] | Me-Meeee, M. M.-M.; Meeee, M. M.; Meeeeee, M., M. Meee. Mee., (8888), 8888. |
[332] | Me-Meeee, M. M.-M.; Meeee, M. M.; Meeeeeeee, M. M., M. Meee. Mee. M, (8888), 8888. |
[333] | Me-Meeee, M. M.-M.; Meeeeeeee, M. M.; Meee-Meeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[334] | Meeeeeeeeee, M.; Meeeee, M.; Meeeeeeeeee, M., M. Me. Meee. Mee., (8888) 88, 888. |
[335] | Meeee, M. M.; Meeeeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[336] | Meeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[337] | Meee, M. M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[338] | Meee, M.; Meee, M.; Meee, M.; Meeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[339] | Meeeeeeeee, M.; Meeee, M.; Meeeeeeeeee, M.; Meeeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.