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Please login to access the full content or check if you have access via39.11.3.1.2.12 Variation 12: Sulfuration with Dimethylthioformamide
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Saito, M.; Nakayama, J., Science of Synthesis, (2008) 39, 620.
In a related procedure to that in Section 39.11.3.1.2.11, dimethylthioformamide reacts with oxiranes, in the presence of a catalytic amount of trifluoroacetic acid in 1,2-dichloroethane, to form the corresponding thiiranes 89 (Scheme 39).[103]
Meeeee 88 Meeeeeeee eeee Meeeeeee Meeee Meeeeeeeeeeeeeeeeeeee[888]
| M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|
| Me | M | 88 | [888] |
| MM8MMe | M | 88 | [888] |
| MM8MMM8MM=MM8 | M | 88 | [888] |
| (MM8)8Me | M | 88 | [888] |
| 8-MeeMMM8 | M | 88 | [888] |
| MM8MMe | M | 88 | [888] |
| MM8MMMM(Me)=MM8 | M | 88 | [888] |
| (MM8)8 | 88 | [888] | |
| (MM8)8 | 88 | [888] | |
Meeeeeee eee eee eeeeeee eeeeeeeeeee ee eeeeeeeeeeee eeeeeeeeee eeeeeeeeeeee eee ee e eeeeee eeeeeeeee eee eeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeee. Meeeeee, eeeee eeeeeeeee eee eeeeeeeeeeeee eeee eeeeee, eeeeeeeeeee eeeeee eeee eeee eeeeeee eeee eee eeeeeeee eeee eeeeee. Meeeeeeeeeee, 8e,8,8,8e-eeeeeeeeeeeeeeeeeeee[8,8-e]eeeeeeee (88) eee ee eeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeee 88 ee eeeeeeeee eeee eeeeeeeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee ee e eeeeeeee (Meeeee 88). Meee eeeeeee eeeeeeeeee eeeeeeeee eeeeee eeee eeee ee eeeee ee eeee eeeeeeeeeee eee 8 eee, eee eeeeeee eeeeeeeee eeee eeeeee ee eee eeeeeee ee −88°M.[888]
Meeeee 88 Meeeeeeee ee 8e,8,8,8e-Meeeeeeeeeeeeeeeeeee[8,8-e]eeeeeeee[888]
Meeeeeeeeeee Meeeeeeee
Meeeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeeeeeeeeeeeeeee:[888]
MMM (8.888 eeee) eee eeeee ee eee eeeeeee (8.88 eeee) eee Me8MMMM (8.8 eeee) ee 8,8-eeeeeeeeeeeeee (88 eM), eee eee eeeeeee eee eeeeeee ee 88°M eee 8 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee ee, eeeeeeeee eeeee (888 eM) eee eeeee, eee eee eeee eee eeeeee eeee M8M (888 eM) ee eeeeee Me8MMMM eee Me8MMMM. Meeee eeeeee (Me8MM8), eee eeeeeeeee eeeee eee eeeeeee eee eee eeeeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee.
8e,8,8,8e-Meeeeeeeeeeeeeeeeeee[8,8-e]eeeeeeee (88):[888]
Me8MMMM (8.888 eM, 8.88 eeee) eee e eeeeeeeee eeeeee ee MM8•MMe8 (8 μM) eeee eeeee ee eee eeeeeee 88 (888 ee, 8.88 eeee) ee MM8Me8 (8 eM) eeee ee −88°M. Mee eeeeeee eee eeeeeee eeeee eee eee eeeeeee eee eeee eeeeeeee [ee. 8 e (MMM (eeeeee eee, eeeeee/MeMMe/Me8M 8:8:8.88)], eee eeee eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee ee −88°M. Mee eeeeeee eee eeeeeeeeeeeeeee eeeeeee e eeeee eeeeee (eeeeee eee, eeeeee/MeMMe/Me8M 8:8:8.88) ee eeeeeee ee eeeeeeee ee eeeeee e eeeeeeeee eeeee; eeeee: 888 ee (88%).
References
| [103] | Meeeee, M.; Meeeeeeee, M.; Meeeeeee, M., Meeeeeeee, (8888), 888. |
| [104] | Meeeee, M.; Meee, M.-M., M. Mee. Meee., (8888) 88, 8888. |
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