[2,3]-Wittig Rearrangements of Difluoroallylic Ethers. A Facile Entry to Highly Functionalized Molecules Containing a CF2 Group

Autor:	S. T. Patel, Robin Wilkes, Jonathan M. Percy
Rok vydání:	1996
Předmět:	chemistry.chemical_compound Primary (chemistry) chemistry Organic Chemistry Wittig reaction Rapid access Molecule Organic chemistry Ether Lithium diisopropylamide Tetrahydrofuran
Zdroj:	The Journal of Organic Chemistry. 61:166-173
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo951516h
Popis:	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.
Databáze:	OpenAIRE
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