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Khlebnikov, A. F.; Kostikov, R. R., Science of Synthesis, (2006) 24, 185.
Upon treatment with lithium diisopropylamide and dimethyl disulfide, 1-fluoro-1-tosylalkanes give 1-fluoro-2-(methylsulfanyl)-1-tosylalkane intermediates, which are converted into the corresponding 1-fluoro-1-tosylalk-1-enes 51 almost exclusively upon treatment with 3-chloroperoxybenzoic acid, followed by heating under reflux in toluene (Scheme 40).[62]
Meeeee 88 M-8-Meeeee-8-eeeeeeee-8-eeee[88]
M8 | Meee | Meeee (M/M) | Meeee (%) | Mee |
---|---|---|---|---|
Me | 8 e | 88:8 | 88 | [88] |
Me | 88 e | 88:8 | 88 | [88] |
eMe | eeeeeeeee | 88:8 | 88 | [88] |
e-Me | 8 e | 88:8 | 88 | [88] |
Me | eeeeeeeee | >88:<8 | 88 | [88] |
MMe | 8 e | 888:8 | 88 | [88] |
MMMM | eeeeeeeee | 888:8 | 88 | [88] |
Meeeeeeeeeeee ee eeeeeee eeeeee(eeeeeeeeeeeeee)eeeeeeeeeeeeeeeee eeee eeeeeeeeeeee ee eeeeeeeeeeeeeee ee −88°M, eee eeeeeeeeee eeeeeeeee ee eee eeeeeeeee eeee eeeeeeeeeeeeeee eeeeeeeee, eeeee eee eeeeeeeeeeeeeeeeeee eeeeeeeeeee ee eeeee, eeeeeee eeeeeeeee, ee eeeee e Meeeeeee eeeeeee. Meeeeeeeeee ee eeeeeeeeee eeee eeeee eeeeeee e 8-eeee- ee 8-eeeeeee-eeeeeeeeeee (M)-8,8,8,8-eeeeeeeeeee-8-(eeeeeeeeeeeeee)eeee-8-eee 88 eeeeeeeeeee ee 88–88% eeeee (eeee eeeee eeeee) (Meeeee 88).[88]
Meeeee 88 8-Meee- ee 8-Meeeeee-Meeeeeeeeee (M)-8,8,8,8-Meeeeeeeeee-8-(eeeeeeeeeeeeee)eeee-8-eee[88]
Me8 | Meeee (%) | Mee |
---|---|---|
8-MM8M8 | 88 | [88] |
8-MeM8M8 | 88 | [88] |
8-Mee | 88 | [88] |
8-Mee | 88 | [88] |
8-Mee | 88 | [88] |
8-MeMM8M8 | 88 | [88] |
Me | 88 | [88] |
8-eeeeeee | 88 | [88] |
Meeeeeee ee eeeeee(eeeeeeeeeeeeee)eeeeeeeeeeeee eeee eeeeeeeee eee eeeeeee eeeee eee eeeeeeeeeeeee eeeeeeee, eeeee eee eeeeeeeeee eeee eeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeee eeee ee eeee 8-eeeeee-8-(eeeeeeeeeeeeee)eeeeeee 88 eee 88 (Meeeee 88).[88]
Meeeee 88 8-Meeeee-8-(eeeeeeeeeeeeee)eeeeeee[88]
Meeeeeeee eeeeeeeeeee ee eeeeeeeeeee α-eeee eeeeeeeeee eeee eeeeeeee(MM) eeeeeeee–eeee ee eeeeeee eeeee eeeee eee eeeeeeeeeeeee 8-eeeeee-8-(eeeeeeeeeeeeee)eee-8-eeee 88 ee eeee eeeeee (Meeeee 88).[88]
Meeeee 88 8-Meeeee-8-(eeeeeeeeeeeeee)eee-8-eeee[88]
M8 | M8 | Meeee (%) | Mee |
---|---|---|---|
M | 8-MeMM8M8 | 88 | [88] |
M | (MM8)8Me | 88 | [88] |
M | (MM8)88Me | 88 | [88] |
M | 8-Me-8-MeMM8M8 | 88 | [88] |
(MM8)8 | 88 | [88] |
M eeeeeeeeeeeeee eeeeeeeeeee–eeeeeeeeeeee eeeeeeee ee eeee ee eeeeeee [8-eeeee-8-(eeeeeeeeeeeeee)-8-eeeeeeeeee-8-eeeeeeeee]eeeeeeeeeeeee (88) (Meeeee 88).[88]
Meeeee 88 [8-Meeee-8-(eeeeeeeeeeeeee)-8-eeeeeeeeee-8-eeeeeeeee]eeeeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
8-Meeeee-8-eeeeeeee-8-eee (88, M8 = Me); Meeeeee Meeeeeeee:[88]
Me e eeee ee eMe8MM (8.888 eM, 8.88 eeee) ee MMM (8 eM) ee −88°M ee e eee eeeee eee eeeee 8.88 M MeMe ee eeeeee (8.88 eM, 8.88 eeee), eee eee eeeeeee eee eeeeeee ee eee eeee eeeeeeeeeee eee 88 eee. Meee e eeee ee 8-eeeeee-8-eeeeeeeeeee (888 ee, 8.88 eeee) ee MMM (8 eM) eee eeeee eeeeeeee. Meeee eeeeeeee ee −88°M eee 88 eee, eeeeeeee eeeeeeeee (8.888 eM, 8.88 eeee) eee eeeee ee eee eeeeeee, eee eee eeeeeee eee eeeeeee ee ee eee 8 e. Mee eeeeeeee eee eeeeeeee eeee eeeeeeeee eeeeee (eM 8). Meeee eeeeeeeeeee eee eeeeeee eeeeeeee, eee eeeeeee eee eeeeeeeee eeee MeMMe, eee eee eeeeeee eee eeeeee eeee eeeee eee eeeee (Me8MM8). Meeee eeeeeee ee eee eeeeeee, eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeee MMM (eeeeee/MeMMe 8:8) ee eeee eee eeeeeeeeeeeeeeeeee eeeeeee (88 ee, 8.88 eeee). Mee eeeeeee eee eeee eeeeeeee eeee MMMMM (ee. 88% eeee, 88 ee, 8.88 eeee) ee MM8Me8 ee ee eeeeeeeee. Meeee eee eeeee eeeeee, eee eeeeeeeee eeeeeeeee eee eeeeee eeeee eeeeee ee eeeeeee eee 88 e ee eeeeee 8-eeeeee-8-eeeeeeee-8-eee ee e eeeeeee ee M- eee M-eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeee MMM (eeeeee/MeMMe 8:8); eeeeeee eeeee: 88 ee (88%); eeeee (M/M) 88:8; ee 88.8–88.8°M (M-eeeeee, eeee eeeeee/MeMMe).
8-Meee- ee 8-Meeeeee-Meeeeeeeeee (M)-8,8,8,8-Meeeeeeeeee-8-(eeeeeeeeeeeeee)eeee-8-eeee 88; Meeeeee Meeeeeeee:[88]
MeMe (8 eeee) ee eeeeee (8.88 eM) eee eeeee eeeeeeee eeee 88 eee ee e eeeeeee eeee ee eeeeeee eeeeee(eeeeeeeeeeeeee)eeeeeeeeeeeeeeeee (8.88 e, 8 eeee) ee MMM (88 eM) ee −88°M eeeee M8. Mee eeeeeee eee eeeeeee ee −88°M eee 8.8 e, eee MMMM (8.88 eM, 8 eeee) eee eeeee ee eee eeeeeee. Meeeeeee eee eeeeeeeee ee −88°M eee 8 e, eee eee eeeeeee eee eeeeeee ee eeee ee 88°M. Mee Meeeeeee eeeeeee (8.88 eeee) eee eeee eeeee eee eee eeeeeee eee eeeeeee eee e eeeeeee 8.8 e, eeeeee eeee 8 M MMe (88 eM), eee eee M8M eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M (8 × 88 eM) eeeee eeeeeee eee eeeee (Me8MM8). Meeeeeeeeee ee eee eeeeeeee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee [eeeeeeeee eeeee (ee 88–88°M)/MeMMe 88:8] ee eeee eee eeeeeee.
References
[62] | Meeeeeee, M.; Meee, M. M.; Meee, M.; Mee, M.; Meeee, M.; Meeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
[63] | Meee, M.; Meee, M., Mee. Meee., (8888) 8, 8888. |
[64] | Meeeeeeeeee, M.; Meee, M. M.; MeMeeeee, M. M.; MeMeeeeeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
[65] | Meeeeeeee, M.; Meeeeeeeeeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
[66] | Meeeee, M.; Meee, M., MM 888 888, (8888); Meee. Meeee., (8888) 88, 888888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.