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Phosphorylation of alkyl-2-chloro-2,3-epoxyalkanoates with trialkyl phosphites: A novel approach to alkyl 2-diethoxyphosphoryloxy-2-alkenoates

✍ Scribed by Tomasz Janecki; Ryszard Bodalski

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 158 KB
Volume: 11
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(2000)11:2<115::aid-hc6>3.0.co;2-6

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✦ Synopsis

Alkyl 2-chloro-2,3-epoxyalkanoates react with trialkyl phosphites to give mixtures of (E) and (Z) alkyl 2-diethoxyphosphoryloxy-2-alkenoates instead of the expected alkyl 2-oxo-3-dialkoxyphosphorylalkanoates. Thermal isomerization of the alkyl 2-chloro-2,3-epoxyalkanoates to alkyl 3-chloro-2-oxoalkanoates and subsequent Perkow reaction of the latter with trialkyl phosphites yields the same products but usually in different (E) to (Z) ratios. A likely mechanism for the unexpected reaction is discussed.

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