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Synthesis, Chemistry, and Characterization of Perfluoroaromatic Selenium Derivatives
Author(s) -
Klapötke Thomas M.,
Krumm Burkhard,
Polborn Kurt
Publication year - 1999
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199908)1999:8<1359::aid-ejic1359>3.0.co;2-c
Subject(s) - chemistry , selenium , halogen , bromine , reagent , sulfuryl chloride , mercury (programming language) , hydrogen peroxide , organic chemistry , trimethylsilyl , organomercury compounds , medicinal chemistry , metal , alkyl , computer science , programming language
The reaction of perfluoroaryllithium RC 6 F 4 Li, where R = F or 4‐CF 3 C 6 F 4 O, respectively, with selenium gives the known diselanes (RC 6 F 4 Se) 2 ( 1a , 1b) . Redox reactions of 1 with hydrogen peroxide result in the formation of the seleninic acids RC 6 F 4 SeOOH which crystallize as hydrates ( 2a , 2b ); with mercury give the bis(arylseleno)mercuries (RC 6 F 4 Se) 2 Hg ( 3a , 3b ); with sulfuryl chloride or bromine give the selenenyl chlorides ( 4a , 4b ) or selenenyl bromides ( 5a , 5b ). Selenenyl chlorides ( 4a , 4b ) react with a variety of trimethylsilyl reagents Me 3 SiX (X = Br, CN, NMe 2 , NEt 2 ) to form 5a , 5b ; selenocyanates RC 6 F 4 SeCN ( 6a , 6b ); selenenyl amides RC 6 F 4 SeNMe 2 ( 7a , 7b ) and RC 6 F 4 SeNEt 2 ( 8a , 8b ). A new synthetic route to diorgano selanes is developed by reaction of 4a , 4b with perfluoroaryllithium to give the symmetric (RC 6 F 4 ) 2 Se ( 9a , 9b ). All derivatives are thoroughly characterized and in addition the molecular structures of 2a , 6a , and 9a are established by X‐ray crystallography.