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Paper | Regular issue | Vol 32, No. 5, 1991, pp.975-984
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5702
Electron Impact Mass Spectra of Some 2’-,3’- and 4’-Substituted Thiophene-2- and 3-Carboxanilides

Cristina Lea Barbieri,* Leopoldo Ceraulo, Paolo De Maria, Antonella Fontana, Domenico Spinelli, and Luca Zuppiroli

*Dipartimento di Chimica Organica "A Mangini", Università degli Studi di Bologna, Via S.Donato 15, 40127 Bologna, Italy

Abstract

The electron impact mass spectra (EI/MS) of 2- and 3-carboxanilides are dominated by the peak due to the corresponding thenoyl cations formed by cleavage of the C-N amide bond. This reaction is not affected by the polar effect of the substituents present in the phenyl ring. Most of the 2’-substituted derivatives undergo a cyclisation reaction with ejection of the substituent. In addition, for 2’-methyl and 2’-ethyl derivatives of both series of thiophene anilides a cryptic "ortho"-effect was suggested as responsible of the charge retention in the aniline moiety.