Header

UZH-Logo

Maintenance Infos

Generation and reactivity of a silylated thiocarbonyl S-methylide


Mloston, G; Urbaniak, K; Linden, A; Heimgartner, H (2007). Generation and reactivity of a silylated thiocarbonyl S-methylide. Heterocycles, 73(1):419-432.

Abstract

The reaction of (trimethylsilyl)diazomethane with methyl (diethoxyphosphonyl)dithioformate (2), after elimination of N2 at –35°C, yields the 4,5-bis(trimethylsilyl)-1,3-dithiolane-2-phosphonate (8). This product is the result of the dimerization of the intermediate silylated thiocarbonyl ylide (4b) to give the cyclic sulfonium ylide (7), followed by the elimination of a disubstituted carbene. Trapping of the intermediate (4b) with maleimide (9), maleic anhydride (10), thiobenzophenone (11), and the phosphonylated dithioformate (2) yields the corresponding [2+3] cycloadducts (12), (13), (14b), and (18), respectively. The crystal structures of 13 and 14b have been established by X-Ray crystallography.

Abstract

The reaction of (trimethylsilyl)diazomethane with methyl (diethoxyphosphonyl)dithioformate (2), after elimination of N2 at –35°C, yields the 4,5-bis(trimethylsilyl)-1,3-dithiolane-2-phosphonate (8). This product is the result of the dimerization of the intermediate silylated thiocarbonyl ylide (4b) to give the cyclic sulfonium ylide (7), followed by the elimination of a disubstituted carbene. Trapping of the intermediate (4b) with maleimide (9), maleic anhydride (10), thiobenzophenone (11), and the phosphonylated dithioformate (2) yields the corresponding [2+3] cycloadducts (12), (13), (14b), and (18), respectively. The crystal structures of 13 and 14b have been established by X-Ray crystallography.

Statistics

Citations

3 citations in Web of Science®
2 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

1 download since deposited on 20 Oct 2011
0 downloads since 12 months
Detailed statistics

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:20 Oct 2011 12:20
Last Modified:05 Apr 2016 15:02
Publisher:Elsevier
ISSN:0385-5414
Funders:Rector of the University of Lodz (grants 505/712 and 505/710), F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.3987/COM-07-S(U)12

Download

Preview Icon on Download
Content: Published Version
Filetype: PDF - Registered users only
Size: 348kB
View at publisher