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Dithio‐ und Thionester, 59. Zur Reaktion von aliphatischen Dithiosäure‐dianionen mit Schwefelkohlenstoff
Author(s) -
Hartke Klaus,
Rettberg Norbert,
Dutta Dinah,
Gerber HansDieter
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301174
Subject(s) - chemistry , deprotonation , medicinal chemistry , adduct , carbon disulfide , yield (engineering) , alkylation , polymer chemistry , organic chemistry , catalysis , ion , materials science , metallurgy
Dithio and Thiono Esters, 59. – Reactions of Aliphatic Dithio Acid Dianions with Carbon Disulfide Dianions 2 of dithioacids 1 and carbon disulfide yield in a kinetically controlled reaction at – 78°C S ‐adducts (e.g. 3 , 13 ) or in a thermodynamically controlled reaction at room temperatur C ‐adducts [the tetrahthiomalonic acid trianions 10 or the 2,2‐dimethyltetrathiomalonic acid dianion 15 ]. Acidification of 10 and subsequent reactions give rise to the tetrathiomalonic acids 18 and its derivatives 19 with 2,6,9,10‐tetrathiaadamantane structure. Deprotonation of 10a leads to the tetrathiomalonic acid tetraanion ( 20 ) which may be alkylated to yield the tetrakis(alkylthio)allenes 21 . By condensation of the dithioacid dianions 2 , the tetrathiomalonic acid trianions 10 and the tetrathiomalonic acid tetraanion ( 20 ) with 2,3‐dichloro‐1,4‐naphthoquinone ( 32 ) a number of naphtho[2,3‐d]‐1,3‐dithiole‐4,9‐diones [e.g. 33 , 35 , 37 ] are obtained.