The chemistry of propargylic and allylic fluorides.
The commonly used methods for the preparation of propargyl monofluorides involve the use of nucleophilic sources of fluorine. The electrophilic sources of fluorine have been used less frequently, however, this strategy shows potential for the expansion of the availability of propargyl monofluorides....
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2008
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| Summary: | The commonly used methods for the preparation of propargyl monofluorides involve the use of nucleophilic sources of fluorine. The electrophilic sources of fluorine have been used less frequently, however, this strategy shows potential for the expansion of the availability of propargyl monofluorides. Very few methods are available for its synthesis because there are difficulties associated with the determination of optical purity and the assignment of absolute configuration. Meanwhile, diethylaminosulfur trifluoride (DAST) is the most widely used reagent for the dehydroxyfluorination of allylic alcohols. The reaction can occur with or without transposition of the double bond and with retention or inversion of configuration. It is found that propargylic fluorides can be used as precursors of allylic fluorides or as dienophiles for the construction of aromatics and heteroaromatics. The discovery of new reactivity of allylic fluorides enhances the understanding of how the fluorine substituent affects reactivity as well as the sense and level of stereocontrol observed ipon manipulation of the adjacent alkene. |
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