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Please login to access the full content or check if you have access via24.2.10.1.4 Method 4: Reaction of Esters of Phosphinous, Phosphonous, and Phosphorous Acids (Michaelis–Arbuzov and Related Reactions)
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Heydt, H., Science of Synthesis, (2006) 24, 448.
The Michaelis–Arbuzov and Michaelis–Becker reactions are standard protocols for the synthesis of acylphosphine oxides, acylphosphinates, and acylphosphonates. Further information may be found in Houben–Weyl, Vols. 12/1, 12/2, E 1, and E 2. The related Perkow reaction involves the synthesis of [1-(organooxy)alk-1-enyl]phosphonates from α-haloketones.[39]
Me eeeeeeeee ee Meeeeee 88.8.88.8.8, eeee eeeeeeeeeeeeeee eeeeeeeee ee eeee eeee eeeeeee eeeeeee, eee eee eeee eee ee eeeeeee eeee eeeeeeee eeeeeeeeeeeee. Meee eeeeeee eeeeeee eeee Meeeeee 88.8.88.8.8 ee eeee eee eeeeeeeeee eeeeeeeee eeeee eee eeeeeeeeee ee 8-eeeeeeeeee-eeeeeeeeeeeeee 8-(eeeeeeeee)eee-8-eeee eeeeeeee, eeeeeee eee eeeeeeeee ee ee eeee eeeeeeeeeeee.
Meee eeeeeee eeeeeeee eeee eeeeeeeeeeeeeeee ee eeeeeeee eeee eeeeeeee eeeeeeeeee (eee Meeeeeeee–Meeeeee eeeeeeee).[88] Me eee eeee ee eeeeeeeeeeee eeeeeeee, ee eee eeee eeeeeeeeeee eeee eee eeeeeeee eeeee ee 88, eeeeee ee eeeeeeee ee 8 eeeeeeeeeee ee eeeeeeeee (Meeeee 88).[88–88] M eeeeeee eeeeeeee ee eeeeeeee ee eeeeeeeeeeeee eeeeeeeee eee eeeeeee ee eeeee eeee eeeeeeee eeeeeeeee ee eeee 88 (Meeeee 88).[88] Meeeeeeee ee eeee 88 eee eeee eeeeeeeeee ee eee Meeeeeeee–Meeeee eeeeeeee ee eeeeeeeeeee eeeeeeee ee eeeeeeeeeeee eeeeeeee eeee eee eeeee ee eeeeeee eeeeeeeeee [MM(M)(MM8)8; M8 = Me (88%), M8 = Me (88%)].[88]
Meeeee 88 Meeeeeeee–Meeeeee Meeeeeee ee Meee Meeeeeeee eeee Meeeeeee Meeeeeeeee[88–88]
Mee eeeeee ee eee eeeeeeee ee ee α,β-eeeeeeeeeee eeee eeeeeeee eeee eeeeeeeee eeeeeeeee eeeeeee eeee eee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeee. Mee eeeeee Meeeeeeee–Meeeeee eeeeeee 88 ee eeeeeeee eeee ee eeeeee ee (M)-eee-8-eeeee eeeeeeee, eeeeeee eeee eeeeeeeee eeeeeeeeee ee eeeeeeeee, eee eeeeee 88 ee eeeeee ee eee eeeee eeeeeee. Mee eeeeeeee (8M)-eee-8-eeeeeeeeeeeeeeee (88) eee eee eeeeeeee (8,8,8-eeeeeeeeee-8-eeeeee-8,8-eeeeeee-8,8λ8-eeeeeeeeeee-8-ee)eeeeeeeeeee (88) eee eeeeeee ee ee eeeeeeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeee ee (M)-Mee-8-eeeee Meeeeeee eeee Meeeeeeee Meeeeeeee[88]
α-Meee eeeeeee eeeee eeee eeeeeeee eeeeeeeeee ee eeee eeee eeeeeeeeee (eee Meeeee eeeeeeee). Me 8-eeeeeeeeee eeeeeeeeeeeeee eeeeee ee eeeeeee ee eeeee eeee eeee(eeeeeeeeeeeeee) eeeeeeeee, eee eee(eeeeeeeeeeeeee) [8-(eeeeeeeeeeeeeee)eeee-8-eeee]eeeeeeeeeee (88) ee eeeeeeee, ee e eeeeeee ee M- eee M-eeeeeee, eeeeeee ee eee eeeeee Meeeee-eeee eeeeeee. Mee eeeeeeee eeeeeeee eeee eeeeeeeee ee e eeeeeeeeeeeeee eeeee eeee eeeeee ee eeeeee (eee Meeee eeeeeeeeeeeee) eee eeeeeeeeeee ee eeeeeeeeeeeeee eeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeee ee 8-Meeeeeeeee Meeeeeeeeeeeee Meeeee eeee Meee(eeeeeeeeeeeeee) Meeeeeeee[88]
8-Meeee-8-eeeeeeeeeeee eee eeee ee eeee ee eee Meeeeeeee–Meeeeee ee Meeeeeeee–Meeeee eeeeeeeee, eeee eeeeeeee eeeeeeeee ee eeeeeee eeeeeeeee, eeeeeeeeeeee. Mee eeeeeeee ee eeeeeeeee eeeeeee ee eeeeee(MM) eeeeeee, ee e eeeeeeeee eeeeeee, ee eeeeeeeee ee eeeeee eeeeeeee (8-eeeeeeeeeeeee)eeeeeeeeeee (88) ee eeee eeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee–Meeeeee Meeeeeee ee 8-Meeee-8-eeeeeeeeeeee eeee Meeeeeee Meeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
Meeeeee {8-[(Meeeeeeeeeeeeeeeee)eee]eeeeeee}eeeeeeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[88]
Me e eeee ee eeeeeeeeeeee eeeeeeee (8.8 eM, 8.88 eee) ee Me8M (88 eM) ee −88°M, eee eeeee e eeee ee M(MMe)8 (88.8 eM, 8.88 eee) ee Me8M (88 eM) ee −88°M. Mee eeeeeee eee eeeeeee ee eeee ee eeeeeee eeeeeeeeeee. Mee MMM eeeeeeee ee eee eeeee eeeee eeeeeee eeeeee eee eeeeeee eee eeeeeeeee eeeeeeeeeeee eeeeeeee. Meeeeeeee eeeeeeeeeeee (ee 888–888/8.8 Meee) eeee eee eeeeeee; eeeee: 88.88 e (88%).
References
[39] | Meeeee, M.; Meeeeee, M.; Meeeee, M.; Meee, M., M. Mee. Meee., (8888) 88, 8888. |
[40] | Meeeeee, M. M., Meee Meee. Meee., (8888) 8, 888. |
[41] | Meeeeeeee, M. M.; Meeeeeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee. Meee, (8888), 88; Meee. Meeee., (8888) 88, 88888. |
[42] | Meeeeee, M. M.; Meeeeeeeeee, M. M., Me. Meeeee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 88, 8888. |
[43] | Meeeeee, M. M.; Meeeee, M. M., Me. Meeeee. Meee., (8888) 88, 8888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 8888. |
[44] | Meee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeee, M., Meeeeeeee, (8888), 888. |
[45] | Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[46] | Meeeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[47] | Meeeeeee, M.; Meeeeee, M.; Meee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[48] | Meee, M.; Meeeeee, M.-M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[49] | Meeeee, M.; Meeee, M. M.; Meeeeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[50] | Meeeeeeee, M. M.; Meeeeeeeeeeee, M. M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 888. |