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Readily undergoes metallation with NaH, n-BuLi, etc. to give a useful formaldehyde anion synthon. Products are readily hydrolyzed by acid./n
Monoalkylation with alkyl halides: Tetrahedron Lett., 3151 (1971), or terminal epoxides leads to the homologated aldehydes: J. Org. Chem., 39, 3645 (1974). Dialkylation with alkyl halides affords, after hydrolysis, symmetrical ketones: Synthesis, 117 (1974). This reaction has also been applied to the synthesis of cyclobutanones and other cycloalkanones: Tetrahedron Lett., 3653 (1974); 2767 (1975). A Knoevenagel reaction with aryl aldehydes gives the ketene thioacetal monosulfoxide, readily solvolyzed in alcoholic HCl to an arylacetic ester: Tetrahedron Lett., 1383 (1972):/n
With ketones, the lithio-derivative gives, after hydrolysis, ɑ-hydroxy aldehydes, not readily available by other routes: Tetrahedron Lett., 2681 (1972). Elimination from the intermediate adduct has also been used as a route to substituted acetic acids: Synthesis, 880 (1979)./n
Hazard Statements: H315-H319
Causes skin irritation. Causes serious eye irritation.
Precautionary Statements: P264b-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362
Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse.