Selective deoxygenation of aryl selenoxides by triaryl phosphites. Evidence for a concerted transformation

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 349-351

  Stratakis, Manolis ^a   Rabalakos, Constantinos ^a   Sofikiti, Nikoletta ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

Mechanisms; Phosphorus acids and derivatives; Selenium and compounds

Indexed keywords

PHOSPHITE; SELENIDE; SELENIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COMPETITIVE BEHAVIOR; KINETICS; MOLECULAR DYNAMICS; OXYGEN TRANSPORT; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE;

EID: 0037421095     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02575-3     Document Type: Article

References (17)

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13. 3 in anhydrous diethyl ether (room temperature, 2 h) containing 5 equiv. of pyridine.
14. 3P=O are as follows. Phosphites: X=H, 128.63; X=F, 128.20; X=Me, 129.18; X=I, 127.16; X=Cl, 127.55; X=OMe, 129.55. Phosphates: X=H, -17.03; X=F, -16.31; X=Me, -16.33; X=I, -17.66; X=Cl, -17.18; X=OMe, -15.33.
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16. Bis(p-methoxyphenyl) selenoxide is commercially available from TCI (Japan).
17. For a previous example of nucleophilic oxygen atom transfer to phosphites, see: Stratakis, M.; Orfanopoulos, M.; Foote, C. S. Tetrahedron Lett. 1991, 32, 863-866.