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Employed in the synthesis of enones by selenenylation of α-cyano ketones with lithium naphthalenide. Phenylselenyl bromide was used in the preparation of exo-2-methyl-7-phenylselenyl-octahydro-8-oxa-2,7b-diaza-dicyclopenta[a,e]pentalene-1,3-dione and endo-2-methyl-7-phenylselanyl-octahydro-8-oxa-2,7b-diaza-dicyclopenta[a,e]pentalene-1,3-dione.
Ali Dondas H, et al. X= Y-ZH Systems as potential 1, 3-dipoles. Part 52: Fused-ring forming electrophile induced oxime?nitrone? cycloaddition cascades. Tetrahedron Lett.2001,57(32), 7035-7045.
Derek H.R. Barton; George Bashiardes; Jean-Louis Fourrey . Studies on the oxidation of hydrazones with iodine and with phenylselenenyl bromide in the presence of strong organic bases; an improved procedure for the synthesis of vinyl iodides and phenyl-vinyl selenides. Tetrahedron,1988, 44(1), 147-162.
Reagent for the introduction of the phenylseleno group. Compare following entry (phenylselenenyl chloride) and Diphenyl diselenide, A13919.
Addition to alkenes gives the kinetic product at low temperature in THF but the thermodynamic product at room temperature in acetonitrile: J. Org. Chem., 42, 2950 (1977):
Hazard Statements: H301-H314-H331-H373
Toxic if swallowed. Causes severe skin burns and eye damage. Toxic if inhaled. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. 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. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant