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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Soluble in methanol.
Notes
Moisture sensitive. Incompatible with strong bases, strong oxidizing agents and strong alkalis.
RUO – Research Use Only
General References:
- 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.