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New applications of hetaryl thioketones for the synthesis of hetaryl-substituted ethenes via ‘two-fold extrusion reaction‘


Mloston, Grzegorz; Urbaniak, Katarzyna; Pawlak, Aneta; Heimgartner, Heinz (2016). New applications of hetaryl thioketones for the synthesis of hetaryl-substituted ethenes via ‘two-fold extrusion reaction‘. Heterocycles, 93(1):127-139.

Abstract

A series of aryl/hetaryl thioketones was applied for the reactions with aryl/hetaryldiazomethanes yielding, after elimination of N2, the corresponding thiiranes. The relatively unstable dihetaryldiazomethanes were generated in situ from the corresponding hydrazones by oxidation with DMSO. The obtained thiiranes were converted into tetraaryl/hetaryl-substituted ethenes in good yields by desulfurization performed with tris(diethylamino)phosphine ((Et2N)3P).

Abstract

A series of aryl/hetaryl thioketones was applied for the reactions with aryl/hetaryldiazomethanes yielding, after elimination of N2, the corresponding thiiranes. The relatively unstable dihetaryldiazomethanes were generated in situ from the corresponding hydrazones by oxidation with DMSO. The obtained thiiranes were converted into tetraaryl/hetaryl-substituted ethenes in good yields by desulfurization performed with tris(diethylamino)phosphine ((Et2N)3P).

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2016
Deposited On:15 Oct 2015 14:45
Last Modified:18 Apr 2018 11:46
Publisher:Elsevier
ISSN:0385-5414
Funders:National Science Center (Cracow, Poland)
OA Status:Green
Publisher DOI:https://doi.org/10.3987/COM-15-S(T)8
Related URLs:https://www.heterocycles.jp/newlibrary/libraries/prepress/special

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