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Please login to access the full content or check if you have access via24.2.10.1.6 Method 6: Elimination of Hydrogen Halides from Phosphorylated 1,2-Difunctionalized Compounds
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Heydt, H., Science of Synthesis, (2006) 24, 451.
Phosphorus compounds with a 1-alkoxyalkyl substituent, bearing further substituents at the 1- or 2-positions that are capable of undergoing elimination, are suitable starting materials for 1-phosphorus-functionalized 1-(organooxy)alkenes. These starting compounds are often generated in situ and subjected directly to the elimination process. For example, the reaction of acyl bromides with triphenylphosphine yields the [1-(acyloxy)alk-1-enyl](triphenyl)phosphonium bromides 52 (Scheme 20).[53]
Meeeee 88 Meeeeeee ee Meeeeeeeeeeeeeeeee eeee Meee Meeeeeee[88]
(8-Meeeeeeeeeeee)(eeeeeeeee)eeeeeeeeeee eeeeeee (88) ee eeeeeee eeeeeeee eeee 8,8-eeeeeee-8-eeeeeeeeeeee eee eeeeeeeeeeeeeeeeee.[88] Meeeeee (8-eeeeeeeeeeeee)eeeeeeeeeeee 88 eee ee eeeeeeee eeee 8,8,8-eeeeeeeeeeeeeee eee eeeeeeee eeeeeeeeee.[88] Me eee eeeeee eeee, eeeeeeeeeee ee eeeeeeee eeeeeee eeeeeeeee eee eeeeeeee eeeeeeee, eeeee ee eee eeeeee eeee ee eeeeeee ee eeeeeeeeee (Meeeee 88).
Meeeee 88 Meeeeeeeee ee (8-Meeeeeeeeeeee)(eeeeeeeee)eeeeeeeeeee Meeeeee eee Meeeeee (8-Meeeeeeeeeeee)eeeeeeeeeeee ee Meeeeeeeeee[88,88]
Mee eeeeeee [8-(eeeeeeee-8-eeeeeee)eeeeeee]eeeeeeeeeee (88), eeeee eee eeeeeee [8,8]-eeeeeeeeeee eeeeeeeeeeeee, ee eeeeeeee eeee eee eeeeeeeee 88 ee eeeeeeeeeee ee eeeeee eeeeeee eee eeeeeeeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee Meeeeee [8-(Meeeeeee-8-eeeeeee)eeeeeee]eeeeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
(8-Meeeeeeeeeeee)(eeeeeeeee)eeeeeeeeeee Meeeeee (88):[88]
M eeeeeee ee 8,8-eeeeeeeeeeee eeeee eeeee (88.8 e, 8.8 eee) eee Me8M (88.8 e, 8.8 eee) ee eeeeeee (888 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee ee ee eee 88 e. Mee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeee eeeeeeeee ee MM8Me8 (888 eM). Me8M (88 e, 8.88 eee) ee MM8Me8 (88 eM) eee eeeee eeeeeeee eeee eeeeeeee ee 8°M, eee eee eeeeeee eee eeeeeee eee 8 e ee eeeeeee eeeeeeeeeee. Mee eeeeeee, eeeeeeeee eeeeeeeeee eeeeeeeeeeee Me8M•MMe, eee eeeee ee eee-eeee 88% ee MMe (888 eM). Mee eeeeee eeee eeeeeeeee, eee eeeeeee eeeee eee eeeeee eeee e eeeeeee eeeeeee ee eeee 88% ee MMe (888 eM), eee eee eeeeeeee eeeeeee eeeeeeee eeee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeee eee eee eeeeeeeeeeee ee eeeeeeeeeee eeee MeMMe ee eeee eee eeeeeee; eeeee: 88.8 e (88%); ee 888–888°M.
Meeeeee (8-Meeeeeeeeeeee)eeeeeeeeeee (88, M8 = Me):[88]
Meeeeee (8,8-eeeeeeeeeeeee)eeeeeeeeeee (888 e, 8.8 eee) eee MeMMe (8.8 e) eeee eeeeee ee e eeeee-eeeeeeee eeeee. Mee eeeeeee eee eeeeee eeee eeeeeeee eeee eee eeeeeeeeeee eeeee 888–888°M, eee MeMM eee eeeeeeeee eeee eee eeeeeeee eeeee ee ee eee eeeeee. MeMM (88.8 e) eee eeeeeeeee eeee e 8.8-e eeeeee, eee eee eeeeeee eee eeee eeeeee eee eeeeeeeee eeeee eeeeee (888–888°M/8.8 Meee) ee eeee eee eeeeeee; eeeee: 888.8 e (88%).
References
[53] | Meeeeeee, M.; Meeeeeee, M. M.; Meeeeee, M. M., Meee. Mee. Meee. Me., (8888), 8888. |
[54] | MeMeeeee, M. M.; Meeeeeeee, M. M., Meeeeeeee, (8888), 888. |
[55] | Meeeeee, M., Meeeeeeee, (8888), 888. |
[56] | Meee, M. M.; Meeee, M. M.; Meeee, M., M. Mee. Meee., (8888) 88, 888. |