Tetrahedron

Competition between addition and redox processes in reactions of Nitroarenes with Lithium-dithianes

G Bartoli, R Dalpozzo, L Grossi, PE Todesco

Index: Bartoli, Giuseppe; Dalpozzo, Renato; Grossi, Loris; Todesco, Paolo E. Tetrahedron, 1986 , vol. 42, # 9 p. 2563 - 2570

Full Text: HTML

Citation Number: 16

Abstract

The reaction of 2-lithio-1, 3-dithianes with nitroarenes gives 2-(or 4-)[(1, 3-dithian)-2'-y1] cyclohexa-3, 5 (or 2, 5-)-diene-1-nitronate compounds (conjugate-addition products), free nitroarene radical anions (redox products), 1, 3-dithianes and 2, 2'-bis-(1, 3-dithianes). The conjugate-addition and redox products were converted in the respective nitroaromatic compounds by oxidation in situ with O2 or DDQ. The ratio between addition and redox ...

Related Articles:

Chemoselective Dithioacetalization and oxathioacetalization of carbonyl compounds using alumina sulfuric acid as catalyst

[Shaterian, Hamid Reza; Hosseinian, Asghar; Ghashang, Majid Synthetic Communications, 2008 , vol. 38, # 23 p. 4097 - 4106]

Highly efficient transdithioacetalization of acetals catalyzed by silica chloride

[Firouzabadi, Habib; Iranpoor, Nasser; Karimi, Babak; Hazarkhani, Hassan Synlett, 2000 , # 2 p. 263 - 265]

2, 4, 4, 6-Tetrabromo-2, 5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS) and bromine as efficient catalysts for dithioacetalization and oxathioacetalization of …

[Iranpoor, Nasser; Firouzabadi, Habib; Shaterian, Hamid Reza; Zolfigol Phosphorus, Sulfur and Silicon and Related Elements, 2002 , vol. 177, # 5 p. 1047 - 1071]

Direct synthesis of 1, 3-dithiane substituted nitroarenes via vicarious nucleophilic substitution with 2-phenylthio-1, 3-dithiane

[Kim, Won-Kyum; Paik, Seung-Chul; Lee, Haiwon; Cho, Cheon-Gyu Tetrahedron Letters, 2000 , vol. 41, # 26 p. 5111 - 5114]

α, α-diacetyl cyclic ketene dithioacetals: Odorless and efficient dithiol equivalents in thioacetalization reactions

[Yu, Haifeng; Liu, Qun; Yin, Yanbing; Fang, Qunxin; Zhang, Jingping; Dong, Dewen Synlett, 2004 , # 6 p. 999 - 1002]

More Articles...