The behaviour of 2-nitrothiophene and of 3-nitrothiophene with some nucleophiles

作者: Carlo Dell'Erba , Marino Novi , Giuseppe Guanti , Domenico Spinelli

DOI: 10.1002/JHET.5570120223

关键词:

摘要: The reactivity of 2-nitrothiophene (1) and 3-nitrothiophene (II) with some nucleophiles has been studied. According to calculated electronic densities I can receive nucleophilic attack at C3 C5 depending on the nucleophile used, but II only C2. With N-lithium piperidine both also give coupling products (VII XI respectively) hithienyl type.

参考文章(26)
Mieczysław Mąkosza, Mikołaj Jawdosiuk, Direct nucleophilic substitution of hydrogen in nitrobenzene with some carbanions J. Chem. Soc. D. ,vol. 0, pp. 648- 649 ,(1970) , 10.1039/C29700000648
Wilhelm Steinkopf, Studien in der Thiophenreihe. XXVII. Über die Bromderivate des 2-Thiotolens European Journal of Organic Chemistry. ,vol. 513, pp. 281- 294 ,(1934) , 10.1002/JLAC.19345130119
C. Dell'Erba, D. Spinelli, G. Leandri, Ring-opening reaction in the thiophen series: reaction between 3,4-dinitrothiophen and secondary amines Journal of The Chemical Society D: Chemical Communications. pp. 549- 549 ,(1969) , 10.1039/C29690000549
Hubert Maag, Badrig K. Manukian, Über das 2‐Nitrothiophen Helvetica Chimica Acta. ,vol. 56, pp. 1787- 1791 ,(1973) , 10.1002/HLCA.19730560539
G. Doddi, G. Illuminati, F. Stegel, Isolation and structure of a Meisenheimer-type compound from a five-membered-ring heteroaromatic substrate Journal of the Chemical Society D: Chemical Communications. pp. 953a- ,(1969) , 10.1039/C2969000953A
Lars Melander, Urs Gloor, Ivan Larsen, Harald Prydz, Calculation of the Directive Influence of a Nitro Group in Position 2 in Thiophene. Acta Chemica Scandinavica. ,vol. 9, pp. 1400- 1401 ,(1955) , 10.3891/ACTA.CHEM.SCAND.09-1400
N. L. Holy, J. D. Marcum, Radical Anion Intermediates in Organic Chemistry Angewandte Chemie International Edition in English. ,vol. 10, pp. 115- 124 ,(1971) , 10.1002/ANIE.197101151