Diethyl Vinylphosphonate

Dedicated to my best friends, Dr. Emilia Obijalska, M.Sc. Marcin Kowalski, M.Sc. Paweł Tokarz, and M.Sc. Aneta Wróblewska.

Introduction

Diethyl vinylphosphonate (1, vinyl phosphonic acid diethyl ester) is a colorless liquid with a characteristic odor, a density of 1.055 g·cm^–3, and a boiling point of 50 °C at one Torr. The synthesis reported by Ford-Moore and Williams in 1947 is still the most convenient preparation.[1] The first step of this procedure consists of an Arbuzov reaction, followed by an elimination of the intermediate ­diethyl 2- bromoethanephosphonate. Diethyl vinylphosphonate is used in Michael-type additions, various metal-supported coupling reactions, cross-metathesis reactions, and in many types of cycloaddition reactions.

Scheme 1

• References

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