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Ethyltriphenylphosphonium bromide acts as a reactant in the synthesis of D-amino acids from L-cysteine-derived thiazolidines, Leiodolide A through aldol reactions and Horner-Wadsworth-Emmons olefination. It is also used in the preparation of cycloalkanoindolines through diastereoselective intramolecular inimo-ene reactions. Further, it is used as a reagent in solid-state metathesis polycondensation to prepare alkyl-dipropenylthiophene monomers and Mizoroki-Heck cyclization and cascading Tsuji-Trost cyclization reactions.
Reaction of the phosphorane (generated using 1 mole of n-BuLi) with an aldehyde at low temperature, followed by a second mole of n-BuLi, gives the -oxido phosphonium ylide which can then be reacted with 1,2-diiodoethane to give (Z)-2-iodo-2-alkenes with high stereoselectivity: J. Chem. Soc., Perkin 1, 1331 (1995). See Appendix 1.
Bagh, F. S. G.; Shahbaz, K.; Mjalli, F. S.; Hashim, M. A.; AlNashef, I. M. Zinc(II) chloride-based deep eutectic solvents for application as electrolytes: Preparation and characterization. J. Mol. Liq. 2015, 204, 76-83.
Harada, K.; Imai, A.; Uto, K.; Carter, R. G.; Kubo, M.; Hioki, H.; Fukuyama, Y. Synthesis of jiadifenin using Mizoroki-Heck and Tsuji-Trost reactions. Tetrahedron 2015, 71 (15), 2199-2209.
Hazard Statements: H301-H319-H500
Toxic if swallowed. Causes serious eye irritation. May form combustible dust concentrations in air
Precautionary Statements: P264b-P270-P280i-P301+P310-P305+P351+P338-P330-P337+P313-P501c
Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear eye/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If eye irritation persists: Get medical advice/attention. Dispose of contents/ container to an approved waste disposal plant