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Takeda, T.; Tsubouchi, A., Science of Synthesis, (2007) 30, 134.
Dithioacetals are prepared from acetals by transthioacetalization with thiols in the presence of acid catalysts, similarly to the thioacetalization of aldehydes and ketones. The transthioacetalization generally enjoys an advantage over the thioacetalization in that the reaction process is more rapid and cleaner. Thus, protic acids, metal salt based Lewis acids, and other Lewis acids are considered as catalysts for this purpose. Without a catalyst, these transformations are carried out by heating the acetals with excess thiols.
Meee eeeeee ee eeeeee eeee eeeeeeeee, 8-eeeeeeeeeeeeeee eeee,[88] eeeeeeee eeeeeeee,[88,88] eee eeeeeeeeeee eeee[88] eee eeeeeeeeee eeeeeeee eee eee eeeeeeeeeeeeeeeeeeeeee ee M,M-eeeeeee ee eeeeeeeeeeeee 8. Meeeeeee eee eeeeeee eeeeeeeeee eee eeeee eeeee (Meeee 8).
Meeee 8 Meeeeeeee ee Meeeeeeeeeeee ee Meeeeeeeeeeeeeeeeeeeee ee M,M-Meeeeee eeee e Meeeee Meee Meeeeeee[88,88–88]
Meeeeeee | M8 | M8 | M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|---|---|
MeMM | M | Me | Me | Me | eeeeeee | 88 | [88] |
MeMM | M | Me | Me | Me | eeeeeee | 88 | [88] |
eee MMe(e) | M | M | Me | Me | 8°M, 8 e, eeee eeeeee, 88 e | 88 | [88] |
MMee | M | Me | Me | Me | MeMM | 88 | [88] |
MMe | M | MMMeMe | Me | Me | MeMM, 88 e | 88e | [88] |
e Meeeeeeee eeee MeMe eee MeMM.
e Me ee M8 eee eeee eeeeeeeeeee eeee MMe.
Meeeeeeeeeeeeeeeeeeeee eeeee eeeee-eeeee Meeee eeeee, eeee ee eeeeeee eeeeeeeeeee,[88,88] eeeeeeeee eeeeeee,[88] eeeeeeee(MMM) eeeeeeeeeeeeeeeeeeeeeeeee,[88] eeeeee(MM) eeeeeeee,[88] eeeeee(MMM) eeeeeeee,[88] eeeeeeee eeeeeeeeeee,[88] ee eeee(MM) eeeeeeee,[88] ee eeeeeeeee eee eeeeeeeeee ee Meeee 8. Mee eeeeeeeeeee ee eeee eeeeeee eeee eeeeeeeeeeeeeeeee ee eeeee ee eee eeee eeee ee eeeeeeee ee eeeeeeee eeee 8,8-eeeeeeeeeeeeeeeeeeeee ee eeeeeee eeee eeeeeeeeeee ee eee eeeeeeee ee eeeeeee eeeeeeeeeee eee 8 eeee, eeeeeee eee eeeeeeeeeeeeeeeeeeeeee ee eee eeeeeee eeeeee eeeeeeee ee eee eeee eeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeeeeeeeee ee eeee eeeee.[88] Meeeeeeee ee eee eeeeeeeeeeeeeeeee ee eeeeeeee eeeeeeeee, eeeee ee e eeeeeeee eeee eeeeeee eeee eeeeeeeee eee eeeeeeeee eeee eeee eeeeeeeeeee eeee eeeee eeee eeeeeee.
MMMMMM: Meeeee eeeeeeeeeee eeeeee ee eeeee eeeeee eee eeeeeeeeeee eee eeeeeeee ee e eeeeeeee ee eeeeeee eeeeeeeeeee ee eeeeeee eeeeeeee eeeee ee eee eeeeeeeeeee eeeeeeeee eeeeee.
Meeee 8 Meeeeeeee ee Meeeeeeeeeeee ee Meeeeeeeeeeeeeeeeeeeee ee M,M-Meeeeee eeee Meeee-Meeee Meeee Meee Meeeeeeee[88,88,88,88,88–88]
Meeeeeee | Meeeeeeeee | Meeeeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
MeMeM8 | 8 M ee Me8M, ee, 88–88 eee | M8 = M; M8 = eMe, Me, 8-MeMM8M8, 8,8-(MeM)8M8M8, MM=MMMe; M8 = Me, Me; M8,M8 = (MM8)8; M8 = Me, Me; M8 = M8 = Me, Me; M8 = Me; M8,M8 = (MM8)8; M8 = Me, Me | 88–88 | [88,88] |
MeMe8 | 8.8 eeeee, Me8M, ee, 88 eee | M8 = M; M8 = Me, (MM8)8Me; M8 = Me; M8 = Me, Me | 88–88 | [88] |
Me(MMe)8 | 8 eee%, [eeee]MM8,e ee, 8–88 eee | M8 = M; M8 = 8-MM8M8 (M = M, Me, MMe), MM=MMMe; M8 = Me, Me, Me; M8 = Me | 88–88 | [88] |
MeMe8 | MMMMe, MeMM | M8 = M; M8 = MMMeMe; M8 = M8 = Me | 88 | [88] |
MeMe8 | 8 eee%, 8,8-eeeeeeeeeeeeee, eeeeee, 8–88 eee | M8 = M; M8 = Me, 8-M8M=MMMM8MM8M8, MM=MMMe; M8 = Me, Me; M8,M8 = (MM8)8; M8 = Me, e-Me, Me; M8 = Me; M8 = eMe; M8 = Me; M8 = Me | 88–88 | [88] |
MeMe8 | MMM, 8°M ee ee, 8 e | M8 = M; M8 = M≡MMe, M≡MMe, M≡M(MM8)8Me; M8 = Me; M8 = Me | 88–88 | [88] |
MeMe8 | Me8M, −88 ee 8°M, 8 e | M8 = M; M8 = 8-(eeeeeeeeeeeeee)eeeeeeeeeee; M8 = Me; M8 = Me | 88 | [88] |
e [eeee]MM8 = 8-eeeee-8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeee.
Meeeeee Meeee eeeee, eeee ee eee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee,[88,88] M-eeeeeeeeeeeeeeee,[88] 8,8,8,8-eeeeeeeeeeeeeeeeeee-8,8-eeeeeee,[88] eee eeeeeeeeeeeeeeeeee eeeeeee,[88] eee eeee eee eee eeeeeeeeeee ee eeeeeee eeeeeeeeeeeee eeee eeeeeee (Meeee 8). Meeee eeee, eee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee ee eeee eeeee eeee eee eee eeeeeeeeeeeeeeeeeeeeee (e.e., eeeeeeeeee ee M,M-eeeeee 88 eeee eeeeeeeeeeee 88, Meeeee 88).[88,88] Meee eeeeeeeeeeeeeeee ee eeeeeeee ee eee M-eeeeeeeeeeeeeeee-eeeeeeee eeeeeeee ee 8-eeeeeeeeeeeeeeeeee eeeeeee eeeeee eeee eeeeeeeeeee ee eee eeeeeeee ee 8-eeeeeeeeeeeeeeeeee; eee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeee ee eeee eeeee eee eee eeeeee ee eeeeeeeee eeeeeeeeeeeeee.[88] Meeeee eeeeeeee, eeeeeeee ee eee eeeeeeeee ee eeeeee eee eeee eeeeeee eeeeeeee, ee eeee eeeeeeee ee e eeeeeeee eee eee eeeeeeeeeeeeee.[88]
Meeee 8 Meeeeeeee ee Meeeeeeeeeeee ee eee Meeeeeeeeeeeeeeeeeeeee ee M,M-Meeeeee Meeee Meeee Meeee Meee Meeeeeeee[88,88,88,88]
Meeeeeee | Meeeeeeeee | Meeeeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
MMM | 88 eee%, MM8Me8, ee, 88–88 eee | M8 = M; M8 = 8-MM8M8 (M = M, Me, MMe), 8-M8MM8M8; M8 = Me, Me, Me; M8 = Me | 88–88 | [88] |
MMMMMe | 88–88 eee%, MMMe8, ee, 88–88 eee | M8 = Me, Me; M8 = Me, 8-Mee; M8 = Me; M8 = Me, Me; M8,M8 = (MM8)88; M8 = M8 = Me | 88–88 | [88] |
MMMM | eeeeeee eeee, 888–888°M, 88–88 eee | M8 = M; M8 = Me, 8-MeMM8M8, 8-M8MM8M8; M8 = Me; M8,M8 = (MM8)8; M8 = Me, Me | 88–88 | [88] |
eeeeee eeeeeeeee | MM8Me8, eeeeee, 88–88 eee | M8 = M; M8 = Me; M8 = Me; M8,M8 = (MM8)8; M8 = Me, Me | 88–88 | [88] |
e MMMMM = 8,8,8,8-eeeeeeeeeeeeeeeeeee-8,8-eeeeeee.
e Meeeeeee eeee eeeeee eee ee eeeeeeeee eeee MMMe8 eee 88 e.
Meeeee 88 Meeee Meeeeeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeeeeee ee Meeeeee[88,88]
Meeeeeeeeeeeeeeeeeeeee ee eeeeeee ee eeeeeeeeeeeee eee eeee ee eeeeeeeee eeeeee ee eeeeeee eeee eeeeee ee eeee 888°M eeeeeee ee eeee eeeeeeee (Meeeee 88).[88–88] Meeee eeee eeeeeeeee, eee eeeee 8,8-eeeeeeee-8-(eeeeeeeeeeeee)eeee-8-ee-8-eee ee eeeeeeeee eeee eee eeeeeeeeeeee 88, ee eeeee eee eeeee eeeeeeeee eeeeeee eeeeeeeee.[88]
Meeeee 88 Meeeeeeee ee Meeeeeeeeeeee ee Meeeeee Meeeeeeeeeeeeeeee ee Meeeeee[88–88]
Meeeeeeeeeee Meeeeeeee
Mee(eeeeeeeeeeeeee)eeeeeee (8, M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[88]
Mee MMe(e) eee eeeeee eeeeeee e eeee ee eeeeeeeeeeeeeeee (88.8 e, 8.888 eee) ee MeMM (888 eM, 8.88 eee) ee 8°M eee 8.8 e eee eee eeee eee eeee eeeeeeee eee 88 e. Meeee eeeeeee, eee MeMM eeeee eee eeeeeeeee. Mee eeeeeeeee eeeeee eeeee eee eeeeee eeee 88% ee MeMM eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eee eee eeeeeee eeeeeeeeeeee ee eeeeeeee ee eeee eee eeeeeee; eeeee: 888 e (88%).
8-[8,8-Mee(eeeeeeeeeeeeee)eeeee]-8-eeeee-8,8,8,8,8,8-eeeeeeeee-8,8-eeeeeeeeeeeeee[8,8-e]eeeeee (88):[88]
MeMM eee eeeeee eeeeeee e eeee ee eeeeee 88 (8 e, 88.8 eeee) ee MM8Me8 (888 eM) eee MM8•MMe8 (88 eM, 888 eeee) eee 88 eee. Mee eeeeeeeee eeee eee eeeeeee eee 88 e ee ee eee eeeeee eeee 88% ee Me8MM8. Meeee eeeeeeee eee 88 eee, eee eeeeeee eeeeeeee eee eeeeeeeee (MM8Me8) eee eeeee. Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee ee eeee eee eeeeeeeeeeee; eeeee: 8.8 e (88%).
References
[12] | Meeeee, M. M., Meeee. Meeeee., (8888) 88, 888. |
[14] | Meeeeeeeeeee, M.; Meeeeeeee, M. M., Mee. M. Mee. Meee., (8888), 8888. |
[15] | Meeeeeeeee, M. M.; Meeeeeeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[18] | Meee, M. M.; Mee, M., Meee. Meee., (8888), 888. |
[20] | Meeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[40] | Meeee, M.; Meeeeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[41] | Meeeeeee, M.; Meeeeeeeeee, M.; Meeeeeeee, M. M.; Meeeeeee, M. M., Meeeeeeeee, Meeeee Meeeeee Meeee. Meee., (8888) 888, 8888. |
[76] | Meee, M.; Meeeeeee, M.; Meeeeee, M.; Meeee, M., Meee. Meee. Mee. Mee., (8888) 88, 888. |
[77] | Meeee, M.; Meeeee, M. M.; Meeeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[78] | Meeeeeeee, M., M. Meee. Mee., (8888), 8888. |
[79] | Meeeeeee, M.; Meee, M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 888. |
[80] | Meee, M. M.; Mee, M.; Meeeeee, M., Meeeeee, (8888), 888. |
[81] | Meeeee, M.; Meeee, M.; Meeee, M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[82] | Meeee, M. M.; Mee, M.-M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[83] | Meee, M.; Meeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[84] | Meee, M.; Meeeee, M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[85] | Meee, M. M.; Mee, M.; Meeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[86] | Meeeeeeeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeeeeeee, M., Meeeeee, (8888), 888. |
[87] | Meeeeeeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 8888; Meee. Meeee., (8888) 88, 8888. |
[88] | Meeeeeeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 8888; Meee. Meeee., (8888) 88, 88888. |
[89] | Meeeeeeee, M. M.; Meeeeeeeeeeee, M. M.; Meeeeeeeee, M. M., Meee. Meee. Meee MMMM, (8888) 888, 888; Meee. Meeee., (8888) 88, 88888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.