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Reactions of 9H-Fluorene-9-thione with (Trimethylsilyl)diazomethane


Mloston, G; Urbaniak, K; Linden, A; Heimgartner, H (2007). Reactions of 9H-Fluorene-9-thione with (Trimethylsilyl)diazomethane. Polish Journal of Chemistry, 81(11):1849-1860.

Abstract

The [3+2]-cycloaddition of (trimethylsilyl)diazomethane (7) with 9H-fluorene-9-thione (1) at –60°C yields the spirocyclic 2,5-dihydro-5-trimethylsilyl-1,3,4-thiadiazole 10, which eliminates nitrogen at room temperature to give the 1,4-dithiane derivative 13 by dimerization of the intermediate fluorenethione (trimethylsilyl)methanide (11). This thiocarbonyl ylide can be trapped by 1 to give the 2-trimethylsilyl-1,3-dithiolane 14 via
[3+2]-cycloaddition. Furthermore, the 1,3-dipole 11 undergoes successfully [3+2]-cycloadditions with the C=S group of the phosphonyldithioformate 15 as well as with the C=C dipolarophiles maleic anhydride (18a) and N-(cyclohexyl)maleimide (18b). The structures of 13 and 14 have been established by X-ray crystallography.

Abstract

The [3+2]-cycloaddition of (trimethylsilyl)diazomethane (7) with 9H-fluorene-9-thione (1) at –60°C yields the spirocyclic 2,5-dihydro-5-trimethylsilyl-1,3,4-thiadiazole 10, which eliminates nitrogen at room temperature to give the 1,4-dithiane derivative 13 by dimerization of the intermediate fluorenethione (trimethylsilyl)methanide (11). This thiocarbonyl ylide can be trapped by 1 to give the 2-trimethylsilyl-1,3-dithiolane 14 via
[3+2]-cycloaddition. Furthermore, the 1,3-dipole 11 undergoes successfully [3+2]-cycloadditions with the C=S group of the phosphonyldithioformate 15 as well as with the C=C dipolarophiles maleic anhydride (18a) and N-(cyclohexyl)maleimide (18b). The structures of 13 and 14 have been established by X-ray crystallography.

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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:2007
Deposited On:07 Nov 2011 13:43
Last Modified:05 Apr 2016 15:04
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Rector of the University of Lodz (grant 505/712), F. Hoffmann-La Roche AG, Basel
Related URLs:http://www.ichf.edu.pl/pjch/pj-2007.htm
http://dx.doi.org/10.1002/chin.200815028

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