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Forms a moderately stable crystalline ylide which reacts with aldehydes to give ɑß-unsaturated nitriles, predominantly as their (Z)-isomers: Chem. Ber., 94, 578 (1961); J. Chem. Soc., 1266 (1961); Appendix 1./n
Further deprotonation of the phosphorane with sodium bis(trimethylsilyl)amide followed by C-alkylation generates a homologated phosphorane: Angew. Chem. Int. Ed., 26, 79 (1987)./n
Reaction of the ylide with carboxylic acids in the presence of EDCI (1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, A10807) and DMAP, followed by ozonolysis of the resulting acylphosphoranes, provides a novel route to the homologous ɑ-keto esters: J. Org. Chem., 59, 4364 (1994):/n
Hazard Statements: H302-H312-H331-H315-H319-H335
Harmful if swallowed. Harmful in contact with skin. Toxic if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.