Open AccessOxidation and reduction of 2,2‐bis(diethylamino)‐2‐ethylium‐1‐dithioate
Author(s) -
Otani Takashi,
Sugihara Yoshiaki,
Ishii Akihiko,
Nakayama Juzo
Publication year - 1998
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/(sici)1098-1071(1998)9:7<703::aid-hc17>3.0.co;2-9
Subject(s) - chemistry , heteroatom , oxidizing agent , reagent , yield (engineering) , bromine , salt (chemistry) , medicinal chemistry , iodide , lithium (medication) , sulfur , photochemistry , inorganic chemistry , organic chemistry , ring (chemistry) , medicine , materials science , metallurgy , endocrinology
Oxidation of the titled inner salt 1 with a typical one‐electron oxidizing reagent, NOPF 6 , produced the radical cation 5a, whose dimerization, followed by loss of a sulfur atom, led to the formation of the bis‐carbenium salt 4a in 95% yield. Moreover, reduction of 1 with a typical one‐electron reducing reagent, lithium naphthalenide, produced the ethene‐1,1‐dithiolate 16, which was converted to the ethene 17 in 73% yield by treatment with methyl iodide. Also reported are synthetic applications of the oxidation of 1 with bromine and the reduction with LiEt 3 BH. © 1998 John Wiley & Sons, Inc. Heteroatom Chem 9: 703–707, 1998