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33.5.1.1.2.1 Variation 1: Michaelis–Arbuzov-Type Reaction

DOI: 10.1055/sos-SD-033-00731

Gaumont, A. C.; Gulea, M.Science of Synthesis, (200733668.

The MichaelisArbuzov-type reaction of trialkyl phosphites with vinyl halides can be used to prepare β-phosphonoacrylates.[‌13‌‌15‌] 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]

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