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Diphenyl diselenide is used in the methoxyselenenylation of alkenes, dihydroxylation of double bonds, hydrothiolation of terminal alkynes. It is used in the synthesis of the unsymmetrical diorganyl selenides, 1-(phenylselenomethyl)vinyl selenides, allylic phenyl selenides.
Akiya Ogawa; Hiroshi Yokoyama; Kazuyuki Yokoyama; Teruyuki Masawaki; Nobuaki Kambe; Noboru Sonoda. Photo-initiated addition of diphenyl diselenide to acetylenes. J. Org. Chem. 1991, 56 (19), 5721-5723.
Brindaban C. Ranu; Tanmay Mandal and Sampak Samanta. Indium(I) Iodide-Mediated Cleavage of Diphenyl Diselenide. An Efficient One-Pot Procedure for the Synthesis of Unsymmetrical Diorganyl Selenides. Org. Lett. 2003, 5 (9), 1439-1441.
Reagent for ɑ-phenylselenation of enolates. The products are readily oxidized to the selenoxides which undergo ambient temperature Cope-type elimination, providing a mild method for the introduction of ɑß-unsaturation into, e.g. ketones: J. Am. Chem. Soc., 97, 5434 (1975):
For a comprehensive review of the preparation of ɑß-unsaturated carbonyl compounds and nitriles by selenoxide elimination, see: Org. React., 44, 1 (1993). Compare also Phenylselenenyl bromide, A11906 and Phenylselenenyl chloride, A12751.
For introduction of the phenylseleno group by Michael addition, phenylselenol can be generated in situ by borohydride cleavage: Synthesis, 664 (1980).
Oxidation of diphenyl diselenide by persulfate in the absence of a nucleophilic counter-ion generates the phenylselenium cation, which adds to alkenes. Molecules with a suitably placed nucleophilic site (alkene, hydroxyl, carbonyl, carboxyl, etc.) can then undergo intramolecular cyclization: J. Org. Chem., 55, 429 (1990); J. Chem. Soc. Perkin 1, 1989 (1993); Synlett, 373 (1994):
For reviews of the application of organoselenium reagents in organic synthesis, see: Tetrahedron, 34, 1049 (1978); Acc. Chem. Res., 12, 22 (1979); 17, 28 (1984). Monograph: Organoselenium Chemistry, D. Liotta, ed., Wiley, N.Y. (1987).
Hazard Statements: H301-H331-H373
Toxic if swallowed. Toxic if inhaled. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P260-P301+P310a-P304+P340-P311a-P405-P501a
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.