Preparation of 3,4-di-t-butylthiophene 1-imide and its N-substituted derivatives

Authors
Otani, T Sugihara, Y Ishii, A Nakayama, J
Citation
T. Otani et al., Preparation of 3,4-di-t-butylthiophene 1-imide and its N-substituted derivatives, TETRAHEDR L, 41(44), 2000, pp. 8461-8465
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
44
Year of publication
2000
Pages
8461 - 8465
Database
ISI
SICI code
0040-4039(20001028)41:44<8461:PO31AI>2.0.ZU;2-G
Abstract
Treatment of 3,4-di-t-butylthiophene 1-oxide with (CF3CO)(2)O or (CF3SO2)(2 )O, followed by reaction with RSO2NH2, ROC(=O)NH2, or RCONH2 furnished a se ries of 1-imino derivatives of 3,4-di-t-butyl-thiophene, which carry an ele ctron-withdrawing substituent on the imino nitrogen atom. Treatment of an i mino derivative (substituent on the nitrogen atom=(CO2Bu)-Bu-t) with CF3CO2 H gave the corresponding aminosulfonium salt, whose deprotonation led to th e N-unsubstituted parent l-imide derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.