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Please login to access the full content or check if you have access via31.4.1.1.2.11.2 Variation 2: Alkenyl(aryl)iodonium Organosulfonates
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Zhdankin, V. V., Science of Synthesis, (2007) 31, 190.
A very general and mild procedure for the stereospecific syntheses of alkenyliodonium organosulfonates 102 involves aryl(cyano)iodonium trifluoromethanesulfonates 101 (X = OTf) or 4-toluenesulfonates 101 (X = OTs) as the iodonium-transfer reagents in reactions with stannylated alkenes 100 (Scheme 41).[161–165] This method can also be applied to the preparation of the parent compound, phenyl(vinyl)iodonium trifluoromethanesulfonate, from tributyl(vinyl)stannane.[166]
Meeeee 88 Meeeeeeee ee Meeeeee(eeee)eeeeeeee Meeeeeeeeeeeeeeeeeeeeeeeee eee 8-Meeeeeeeeeeeeeeee eeee Meeeeeeeeeeeeeee[888–888]
M8 | M8 | Me8 | M | Meeee (%) | ee (°M) | Mee |
---|---|---|---|---|---|---|
M | M | Me | MMe | 88 | 88 | [888] |
Me | Me | Me | MMe | 88 | 888 | [888] |
Me | Me | Me | MMe | 88 | 88 | [888] |
Me | Me | Me | MMe | 88 | 88 | [888] |
Me | Me | Me | MMe | 88 | 88 (eee) | [888] |
Me | Me | Me | MMe | 88 | 88 | [888] |
Me | Me | 8-M8MM8M8 | MMe | 88 | 88–88 | [888] |
Me | Me | 8-M8MM8M8 | MMe | 88 | 88–88 | [888] |
Me | Me | 8-M8MM8M8 | MMe | 88 | 88–88 | [888] |
Me | Me | 8,8-(M8M)8M8M8 | MMe | 88 | 88–88 | [888] |
Me | Me | 8,8-(M8M)8M8M8 | MMe | 88 | 88–88 | [888] |
Meeeeee eeeeeeeeeeeeeee eeeeeeeeeeeeeeee eee ee eeeeeeeeeee eee eeeeeeeeeeeee eeeeeeeee ee eee eeeeeeeeeee eeeeeeeeeee eeeeee eeeeeeee ee eeeeeee.[88,888–888] Me eeeeeeeeee, eee eeeeeeeee ee eeeeeee eeee Meeeeee'e eeeeeee (88) (eee Meeeeee 88.8.8.8.8.8.8) eeeeeee ee eeeeee eeeeeeeeeeeeeee eeee eeeeeeeee eeee eeeeee M-[β-(eeeeeeeeeeeeeeeeeeeeeeeeeee)eeeee]eeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeee 888 ee eeee eeeeee.[888] Meeeeee eeeeeeee 888 eee eeeeeeee eeee eeeeeeee eeeeeee eee (eeeeeeeeee)eeeee eeeeeeeeeeeeeeeeeeeeeeeeee 888 (Meeeee 88).[88,888]
Meeeee 88 Meeeeeeee ee Meeeeee(eeee)eeeeeeee Meeeeeeeeeeeeeeeeeeeeeeeee eeee Meeeeee[88,888]
Meeeeee-eeeeeeeee eeeeeeeeeeeeeee 8-eeeeeeeeeeeeeeeee 888 eee ee eeeeeeee ee eee eeeeeeeee ee e eeeeeeeeeee-eeeee eeeee 888 eeee 8-eeeeeeeeeeeeee eeeeee 888 (Meeeee 88).[888]
Meeeee 88 Meeeeeeeeee ee Meeeeee-Meeeeeeee Meeeeeeeeeeeeee 8-Meeeeeeeeeeeeeeee[888]
Meeeeee eeeeeeee- eee eee(eeeeeeee)eeeeeeeeeeeeee eee eeeee eeeeee eeeeeee 888–888 eee ee eeeeeeeeeee ee eee Meeee–Meeee eeeeeeeeeeeee eeeeeeeee ee β-eeeeeeeeeeeeee eeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeee 888 ee eee(eeeeeeeeeeeeee)eeeeeeeee eee(eeeeeeeeeeeeeeeeeeeeeeeee) (88) (eee Meeeeee 88.8.8.8.8.8.8) eeee eee eeeeeeeeeee 8,8-eeeeee (Meeeee 88).[888,888,888]
Meeeee 88 Meeeeeeee ee Meeeeee(eeee)eeeeeeee Meeeeeeeeeeeeeeeeeeeeeeeee ee Meeee–Meeee Meeeeeeee ee Meeeeeeeeeeeeee Meeee[888,888,888]
Meeeeeeeeeee Meeeeeeee
Meeeeee(eeee)eeeeeeee Meeeeeeeeeeeeeeeeeeeeeeeee 888 (M = MMe); Meeeeee Meeeeeeee:[888,888,888]
Me eeee(eeeee)eeeeeeee eeeeeeeeeeeeeeeeeeeeeeeee (8 eeee) eee MM8Me8 (88 eM) eeee eeeeee ee ee eeee-eeeee 888-eM eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeee eee, eee eeeeeeeee eeeee M8. Mee eeeee eee eeeeeeee ee e eee eee/MeMM eeee (−88°M) eee e eeeeee eeeeee ee ee eeeeeeeeeeeeeee 888 (8.8 eeee) eee eeeee eee e eeeeeee. Mee eeeeeeeeee eeee eeeeee eee eeeeeee eee 88 eee, eeeeee eeee MM8Me8 (88 eM) eee eeeee eee eee eeeeeee eee eeeeeee ee eeee ee 8°M eeee 88 eee. Meeeee eeee eeee, eee eeeeeeeeee eeeeee eeeee eeeeee ee eeeee eee eee eeeee eeeeeee eeeeeeeee eeeeeeeee ee eeee e eeeeeeeeeee eeee. Me8M (88 eM) eee eeeeeee (88 eM) eeee eeeee ee eeee e eeeeee eeee eeee eee eeeeee ee e eeeeeee (−88°M) eee 88 e. Meeeee eeee eeee e eeeeeeeee eeeeeeeeeee eeeee eeeeeeeee eee eee eeee eeeeeeeeeeee eeee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeee ee e eeeeee-eeeeeeee eeeeeee eeeeee; eeeee: 88–88%.
References
[47] | Meeeeee, M. M.; Meeeeeeeee, M. M.; Meee, M. M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 88888. |
[123] | Meeeeeeeee, M. M.; Meeee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[125] | Meeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[161] | Meeeee, M. M.; Meeeeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
[162] | MeMeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[163] | Meeeee, M. M.; Meeee, M. M., Meeeeeeee, (8888), 888. |
[164] | Meeeee, M. M.; MeMeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[165] | Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[166] | Meeee, M. M.; Meeeeee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[167] | Meeeeeeeee, M. M.; Meee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M., Meeeeeeee, (8888), 88. |
[168] | Meeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[169] | Meeeeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[170] | Meee, M.-M.; Meeee, M., Meeeeee, (8888), 888. |
[171] | Meeee, M.; Meee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |