Readily prepared primary, secondary, and tertiary difluoroallylic
alcohols, derived from commercially
available and inexpensive 2,2,2-trifluoroethanol, have been transformed
into a range of difluoroallylic
methyl ethers containing appropriate carbanion-stabilizing
substituents. The [2,3]-Wittig rearrangements of these difluoroallylic ethers have been achieved cleanly,
using lithium diisopropylamide in tetrahydrofuran at −30 °C, in excellent (secondary ether
substrates) to good (primary
and tertiary ether substrates) yields. Consequently, the approach
allows convenient and rapid
access to products containing a mid-chain CF2 group
and with a useful level of functionality.
Ethers of a difluoroallylic alcohol undergo clean, high-yielding [2,3]-Wittig rearrangements in tetrahydrofuran (THF) at -3O"C, affording highly functionalised products with an in-chain difluoromethylene group.
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