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Ipso nitration. Nitrodeformylation reactions in nitrothiophenealdehydes
Author(s) -
Cogolli Pietro,
Maiolo Filippo,
Testaferri Lorenzo,
Tiecco Marcello,
Tingoli Marco
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160741
Subject(s) - nitration , chemistry , nitro , nitro compound , organic chemistry , medicinal chemistry , alkyl
Abstract Nitration of 4‐nitro‐2‐thiophenealdehyde afforded 2,4‐dinitrothiophene and small quantities of 4,5‐dinitro‐2‐thiophenealdehyde; 5‐nitro‐2‐thiophenealdehyde gave instead 3,5‐dinitro‐2‐thiophenealdehyde as the main product and some 2,5‐dinitrothiophene. The two dinitrothiophenes form through a nitrodeformylation reaction which represents an interesting example of the nitration at an ipso position in a strongly deactivated substrate.