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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):
Gefahrenhinweise (EU): H301-H331-H373
Toxic if swallowed. Toxic if inhaled. May cause damage to organs through prolonged or repeated exposure.
Do not breathe dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER/doctor. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.