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Eur. J. Mass Spectrom. DOI: 10.1255/ejms.618

Cyclization of N,N-dialkylditiocarbamate and alkylxanthate derivatives of polyhalogenated pyridines in gas and liquid phases

TatianaYu.Samguina, Vladislav V.Lobodin, Nadezhda K.Karakhanova and Albert T.Lebedev
Organic Chemistry Department, Moscow State University, Leninskie gori, 1/3, Moscow, 119899, Russia E-mail:
Aleksey M. Sipyagin
Institute of Problems of Chemical Physics RAS, Chernogolovka, 142432, Russia

ABSTRACT:
The intramolecular cyclization of 31 polyhalogen substituted pyridines containing N,N-dialkyldithiocarbamate or alkylxanthate groups has been compared in reaction in solution with sodium N,N-dialkyldithiocarbamates or potassium carbetoxydithiolate and in the gas phase under electron ionization (EI). The scheme of fragmentation of the studied compounds has been proposed. An influence of the nature of leaving groups (Cl, F, CF3, CN, COOEt), of the presence of electron withdrawing groups (Cl, F, CN, CCl3, CF3, COOEt) in ortho-, meta or para-positions to the leaving halogen, of the position of a dithio group toward pyridine nitrogen atom and of the role of oxygen and nitrogen in corresponding alkylxanthates and N,N-dialkyldithiocarbamates on the cyclization process has been investigated.

Keywords: derivatives of polyhalogenated pyridines, electron ionization, cyclization in the gas phase

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