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Please login to access the full content or check if you have access via33.5.1.1.2.1 Variation 1: Michaelis–Arbuzov-Type Reaction
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Gaumont, A. C.; Gulea, M., Science of Synthesis, (2007) 33, 668.
The Michaelis–Arbuzov-type reaction of trialkyl phosphites with vinyl halides can be used to prepare β-phosphonoacrylates.[13–15] Trialkyl phosphites and 2-chlorovinyl ketones give (3-oxoalk-1-enyl)phosphonates, enol phosphonates, and (3-oxoalkyl)-1,1-bisphosphonates.[16] The addition of a dialkyl trimethylsilyl phosphite 4, generated in situ from the corresponding dialkyl phosphite, to α-haloacrylates 5 gives the trans β-phosphonoacrylates 6 efficiently and stereoselectively under mild conditions (Scheme 4).[14]
Meeeee 8 Meeeeeeeeee ee Meeeeee β-Meeeeeeeeeeeeeeeee ee (Meeeeeeeee)eeeeeeeeeeee ee Meeeeeeee–Meeeeee Meeeeeee[88]
Meeeeeeeeeee Meeeeeeee
Meeeeee [(M)-8-Meeeeeeeee]eeeeeeeeeee (8, M8 = Me; M8 = MM); Meeeeee Meeeeeeee:[88]
MMMMe (8.88 eM, 8.88 eeee, 8.8 eeeee) eee eeeee ee e eeeeeee eeee ee (MeM)8M(M)M (8.88 e, 8.88 eeee) eee Me8M (8.88 eM, 8.88 eeee, 8.8 eeeee) ee MM8Me8 (88 eM) eee eee eeeeeee eee eeeeeeeeee ee 8°M eeeee eeeee eee 88 eee. 8-Meeeeeeeeeeeeeeeeee (8.88 e, 8.88 eeee) eee eeee eeeee eee eee eeee eee eeeeeee ee ee. Meeee 8 e, eee eeeeeee eee eeeeee eeee M8M (88 eM) eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eeeeee eeee eeeee eee eeeeeeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeeee ee Meeeeeeee eeeeeeeeeeee (888°M/8.8 Meee) ee eeee e eeeeeeeee eeeeee; eeeee: 8.88 e (88%).
References
[13] | Meeee-Meee, M. M.; Màeeee-Meeee, M.; Meeeeeeee-Meeeee, M.; Meeeeeeee, M., M. Mee. Meee., (8888) 88, 88. |
[14] | Meeeeeeee, M.; Meeee, M.; Meeeee, M. M. M.; Meeeeee-Meeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
[15] | Meeeeee, M., Meeeeeeeee Meeeee Meeee. Meee., (8888) 88, 888. |
[16] | Meeeeeeeeeeee, M.; Meeeee, M., Meeeeee Mee. Meee., (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.