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

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作者：

LV Klyba，OA Tarasova，L Brandsma，NA Nedolya，KB Petrushenko

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摘要：

Triads of isomeric N -alkyl- N -methyl-3-phenylthiophen-2-amines, N -methyl-3-alkyl-4-methylidene-3-phenylthietan-2-imines, and N -methyl-4-alkylsulfanyl-2-phenylcyclobut-2-en-1-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 α-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 1-alkyl-1-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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关键词：

cinnamic acid isoflavones synthesis

DOI：

10.1134/S107042800607013X

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年份：

2006