I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Phenylselenenyl chloride is used in the preparation of (cyclobut-1-enylselanyl)benzene. It is an important versatile reagent used in organic synthesis. Further, it serves as a useful synthon for 2-amino alcohols.
ɑ-Phenylselenoketones can be prepared, e.g. by reaction of Li enolates with phenylselenenyl halides, and conversion to the corresponding unsaturated ketones by selenoxide elimination: J. Am. Chem. Soc., 97, 5434 (1975). Oxidizing agents include H2O2, mCPBA or periodate. For application to ß-diketones, see: Org. Synth. Coll., 6, 23 (1988):
ß-Keto lactones undergo a similar sequence to give unsaturated lactones: J. Org. Chem., 46, 2920 (1981). -Lactones can be converted to dihydrofurans and thence to furans: J. Org. Chem., 40, 542 (1975). Similarly, cyclohexenones can be aromatized to phenols by selenenylation of the enolate and oxidation with mCPBA: Tetrahedron Lett., 23, 51 (1982). For a comprehensive review of the preparation of ɑß-unsaturated carbonyl compounds and nitriles byselenoxide elimination, see: Org. React., 44, 1 (1993).
Adds to alkenes to give trans-chloroselenylated dervatives via a selenium bridged cation: J. Org. Chem., 39, 428 (1974); Tetrahedron Lett., 4977 (1978). Also widely applied in cyclization of various molecules containing olefinic double bonds, e.g. unsaturated alcohols undergo seleno-etherification: J. Am. Chem. Soc., 102, 3784 (1980); Tetrahedron Lett., 31, 5917 (1990).
δ-Unsaturated ketones undergo cyclofunctionalization, providing access to vic-functionalized cyclopropanes and oxygenated heterocycles: Synlett, 965 (1994):
Reacts with alkenylboronic acids in ionic liquids to give (Z) and (E) vinyl selenides: Tetrahedron Lett., 43, 373 (2002).
Tancock, J.; Wirth, T. Selenium-Mediated Synthesis of Tetrasubstituted Naphthalenes through Rearrangement. Molecules 2015, 20 (6), 10866-10872.
U. A. Kshirsagar. Recent developments in the chemistry of quinazolinone alkaloids. Org. Biomol. Chem. 2015, 13 (36), 9336-9352.
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.