You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via21.14.1.1.1 Method 1: The Arbuzov Reaction: Acylation of Phosphorus(III) Compounds
Please login to access the full content or check if you have access via
Whitehead, A.; Sieck, S. R.; Mukherjee, S.; Hanson, P. R., Science of Synthesis, (2005) 21, 907.
The most general approach to this subclass of compounds is the Michaelis–Arbuzov reaction of trialkyl or triaryl phosphites with acyl chlorides; it remains the most widely employed route for the generation of acylphosphonates (see Sections 21.14.1.2.1.3, 21.14.1.2.2.3, 21.14.1.2.3.1, 21.14.1.2.7, and 21.14.1.2.7.2). While having been extensively studied, areas of interest remain. One area of continued investigation is the generation of nonsymmetrically substituted acylphosphonates from mixed phosphite precursors.[4] This method requires differentiated reactivity between the different phosphite substituents. For example, treatment of benzyl dimethyl phosphite (1) with an acid chloride gives a mixture of symmetric and nonsymmetric acylphosphonates, separable by distillation, resulting in the nonsymmetric acylphosphonate 2 in moderate yield (Scheme 1).[4]
Meeeee 8 Meeeeeeeeeee Meeeeeeeeeeeeeee eee eee Meeeeee Meeeeeee[8]
Meeeeeeeeeee Meeeeeeee
Meeeee Meeeee Meeeeeeeeeeeeeee 8; Meeeeee Meeeeeeee:[8]
Me eeee eeeeeeee (8 eeeee) eee eeeee ee eeeeee eeeeeeee eeeeeeeee (8; 8 eeeee) eeeee e eeeeee ee M8 (MMMMMMM: eee eeeeeeee ee eeee eeeeeeeeee), ee e eeeeeeeeeee eeeeeeeeee eeeeeee −88 eee 8 ºM. Me eee eee ee eee eeeeeeee, eee eeeeeee eee eeeeeee eee 8 e ee ee eeeee eee eeeee eeeeeeee eee eeeeeeeeee eeeeeeee. Mee eeeeeeeee eeeeeeeeeeeeeee, M8MMMM(MMe)8, eee eeeeeeeee eee ee eeeeeeeeeeee. Mee eeeeeeeeeeee eeeeeeeeeeeeeee 8 eee eeee eeeeeeeee eeee Me8M, eee eeeeeeeee ee eee eeee ee e eeeeeeeee eeeeee eeee eeeeeee ee eee eeeeeee; eeeee: ee. 88%.
References
[4] | Meeeee, M. M.; Meeeeee, M.; Me Meeeeee, M.; Meeeee, M., Meeeeeeeee, Meeeee Meeeeee Meeee. Meee., (8888) 888, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 8888.