Studies of the Synthesis of Diethyl Cyclopropylphosphonate and Its Thio and Seleno Analogs |
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Authors: | Yossi Zafrani Ravit Chen Nissan Ashkenazi Yoffi Segall |
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Institution: | 1. Department of Organic Chemistry , Israel Institute for Biological Research , Ness‐Ziona, Israel zafrani@iibr.gov.il;3. Department of Organic Chemistry , Israel Institute for Biological Research , Ness‐Ziona, Israel |
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Abstract: | Two methods for the synthesis of unsubstituted diethyl cyclopropylphosphonate are described. One method is a reaction between cyclopropylmagnesium bromide and diethyl chlorophosphite to give diethyl cyclopropylphosphonite, followed by oxidation with sodium periodate to the corresponding phosphonate. Alternatively, diethyl cyclopropylphosphonite was reacted with elemental sulfur or selenium to give the thio and seleno analogs, respectively. The second method involves exclusive 1,3‐elimination of HBr from diethyl 3‐bromopropylphosphonate. This method can be directed to either the 1,2‐ or the 1,3‐elimination reaction, leading to propenylphosphonate or cyclopropylphosphonate, depending on the solvent used. |
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Keywords: | bromopropylphosphonate cyclopropylmagnesium bromide diethyl cyclopropylphosphonate |
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