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Author(s): Klyba LV; Tarasova OA; Brandsma L; Nedolya NA; Petrushenko KB
Title: A new approach to the synthesis of strained cyclic systems: II. Mass spectrometric study of 2-dialkylamino-3-phenylthiophenes and their structural isomers, iminothietanes and iminocyclobutenes
Source: RUSSIAN JOURNAL OF ORGANIC CHEMISTRY 42 (7): 1003-1014
Date: 2006 JUL
Document Type: Journal : Article
DOI:
Language: English
Comment:
Address: Russian Acad Sci, Favorskii Irkutsk Inst Chem, Siberian Div, Irkutsk 664033, Russia.
Univ Utrecht, Utrecht, Netherlands. Reprint: Klyba, LV, Russian Acad Sci, Favorskii Irkutsk Inst Chem, Siberian Div,
Ul Favorskogo 1, Irkutsk 664033, Russia. E-mail: klyba@irioch.irk.ru
Abstract: Triads of isomeric N-alkyl-N-methyl-3-phenylthiophen-2-amines, N-methyl-3-alkyl4-methylidene3-phenylthietan-2-imines, and N-methyl-4-alkylsulfanyl-2-phenylcyclobut-2-en-l-imines (Alk = Me, Et, Bu) were synthesized from 1,3-dilithio-3-phenylpropyne, methyl isothiocyanate, and alkyl halides, and their fragmentation under electron impact was studied. Primary decomposition of the molecular ions of 2-aminothiophenes is determined by the localization of a radical cation center on the nitrogen atom, and it follows a path typical of alkyl(aryl)amines with elimination of hydrogen atom or methyl or propyl radical from the a-carbon atom in the N-alkyl substituent. Fragmentation of the iminothietanes involves cleavage of the four-membered ring in half to give neutral MeNCS molecule and l-alkyl-l-phenylallene radical cation. Alkylsulfanyl(imino)cyclobutenes undergo cleavage at the sulfur-containing side chain according to general relations holding in the fragmentation of alkyl sulfides.
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