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Synthesis 2003(5): 0685-0690
DOI: 10.1055/s-2003-38070
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis, Characterization and Crystallographic Studies of Three 2-Aryl-3-methyl-4-aryl-1,3-thiazolium-5-thiolates

Petronio Filgueiras de Athayde-Filho*a,b,c, Joseph Miller*b,c, Alfredo Mayall Simasc, Bruno Freitas Lirab,c, José Alixandre de Souza Luisb, Júlio Zuckerman-Schpectord
a Universidade Federal da Paraíba, Departamento de Ciências Básicas Sociais - Bananeiras - PB and Departamento de Química, João Pessoa - PB, 58051-970, Brasil
e-Mail: athayde-filho@uol.com.br;
b Universidade Federal da Paraíba, Laboratório de Tecnologia Farmacêutica
e-Mail: millerjo@ltf.ufpb.br;
c Universidade Federal de Pernambuco, Departamento de Química Fundamental, Recife - PE, 50670-901, Brasil
e-Mail: ams@npd.ufpe.br;
d Universidade Federal de São Carlos, Laboratório de Estereodinâmica e Modelagem Molecular, São Carlos - SP, 13565-905, Brasil
e-Mail: julio@power.ufscar.br;
Further Information

Publication History

Received 4 December 2001
Publication Date:
21 March 2003 (online)

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Abstract

Mesoionic 2,4-diphenyl-3-methyl-1,3-thiazolium-5-thiolate, 2-(4′-chlorophenyl)-3-methyl-4-phenyl-1,3-thiazolium-5-thiolate and 2-(4′-chlorophenyl)-3-methyl-4-(4′-isopropyl-phenyl)-1,3-thiazolium-5-thiolate were synthesized via N-methyl-C-aryl-glycines, involving a one-pot 1,3-dipolar cycloaddition/cycloreversion sequence. The two latter mesoionic compounds are new, as are some of the intermediates. Compounds were fully characterized, while X-ray diffraction studies of the three mesoionic compounds also confirmed their structures and our definition of mesoionic compounds. In particular they showed that the mesoionic ring system has two regions in which there is electron and charge delocalization separated by what are essentially single bonds. The data also suggested a tendency for the 2- and 4-aryl groups to lie in the plane of the mesoionic ring.

Key words

mesoionic - betaine - 1,3-thiazolium-5-thiolates - synthesis - crystallography

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