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Wittig reaction (see Appendix 1) with aldehydes, using K2CO3 in toluene, gives dienes: Synth. Commun., 22, 1421 (1992). The derived phosphorane also reacts with ß-chloroacrylates to give conjugated phosphoranes, convertible to trienes: Tetrahedron Lett., 1359 (1975):/n
Michael addition of the phosphorane to ɑß-unsaturated ketones, followed by intramolecular Wittig reaction, gives cyclohexa-1,3-dienes: Tetrahedron Lett., 4425 (1973). Further lithiation of the phosphorane in the presence of TMEDA, followed by reaction of the ylide anion with an aldehyde, provides a route to (E,E)-ß-hydroxy-1,3-dienes: Tetrahedron Lett., 32, 4353 (1991)./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