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Alkylating agent for introduction of the trifluoroethyl group./n
Metallation by LDA leads to 2,2-difluoro-1-tosyloxyvinyllithium, which adds quantitatively to carbonyl groups. Acid hydrolysis leads to ɑ-tosyloxy acrylates, which can be hydrolyzed to ɑ-keto acids by base: Tetrahedron Lett., 4809 (1978):/n
n-BuLi at -78o has also been used by Ichikawa's group to generate the vinyllithium intermediate, which undergoes boron or copper mediated reactions yielding 2,2-difluorovinyl ketones and other products. See, e.g.: Tetrahedron Lett., 33, 337 (1992); Tetrahedron, 50, 11637 (1994); J. Org. Chem., 60, 2320 (1995)./n
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant