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Syntheses and Reactions of Hexavalent Organotellurium Compounds Bearing Five or Six TelluriumCarbon Bonds
Author(s) -
Miyasato Masataka,
Sagami Takao,
Minoura Mao,
Yamamoto Yohsuke,
Akiba Kinya
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305260
Subject(s) - chemistry , stereochemistry , medicinal chemistry
A variety of hexaorganotellurium compounds, Ar 6− n (CH 3 ) n Te [Ar=4‐CF 3 C 6 H 4 , n =0 ( 1 a ), n =1 ( 3 a ), n =2 ( trans ‐ 4 a and cis ‐ 4 a ), n =3 ( mer ‐ 5 a ), n =4 ( trans ‐ 6 a ); Ph, n =0 ( 1 b ), n =1 ( 3 b ), n =2 ( trans ‐ 4 b ); 4‐CH 3 C 6 H 4 , n =0 ( 1 c ), n =1 ( 3 c ), n =2 ( trans ‐ 4 c ), n =4 ( trans ‐ 6 c ); 4‐BrC 6 H 4 , n =0 ( 1 d )] and Ar 5 (R)Te [Ar=4‐CF 3 C 6 H 4 , R=4‐CH 3 OC 6 H 4 ( 8 ); Ar=4‐CF 3 C 6 H 4 , R=vinyl ( 9 ), Ar=Ph, R=vinyl ( 10 ), Ar=4‐CF 3 C 6 H 4 , R=PhSCH 2 ( 11 ), Ar=Ph, R=PhSCH 2 ( 12 ), Ar=4‐CF 3 C 6 H 4 , R= n Bu ( 13 )] and pentaorganotellurium halides, Ar 5 TeX [Ar=4‐CF 3 C 6 H 4 , X=Cl ( 2 a ‐Cl), X=Br ( 2 a ‐Br); Ar=Ph, X=Cl ( 2 b ‐Cl), X=Br ( 2 b ‐Br); Ar=4‐CH 3 C 6 H 4 , X=Cl ( 2 c ‐Cl), X=Br ( 2 c ‐Br); Ar=4‐BrC 6 H 4 , X=Br ( 2 d ‐Br)] and (4‐CF 3 C 6 H 4 ) 4 (CH 3 )TeX [X=Cl ( trans ‐ 7 a ‐Cl) and X=Br ( trans ‐ 7 a ‐Br)] were synthesized by the following methods: 1) one‐pot synthesis of 1 a , 2) the reaction of SO 2 Cl 2 or Br 2 with Ar 5 Te − Li + generated from TeCl 4 or TeBr 4 with five equivalents of ArLi, 3) reductive cleavage of Ar 6− m (CH 3 ) m Te ( m= 0 or 2) with KC 8 followed by treatment with CH 3 I, 4) valence expansion reaction from low‐valent tellurium compounds by treatment with KC 8 followed by reaction with CH 3 I, 5) nucleophilic substitution of Ar 6− y − z (CH 3 ) z TeX y − z (X=Cl, Br, OTf; z =0, 1; y =1, 2) with organolithium reagents. The scope and limitations and some details for each method are discussed and electrophilic halogenation of the hexaorganotellurium compounds is also described.