UZH-Logo

Maintenance Infos

Synthesis of hetaryl-substituted 1,2,4-trithiolanes via a three-component reaction with dihetaryl thioketones, benzyl azide, and 2,2,4,4-tetramethyl-3-thioxocyclobutanone


Mloston, Grzegorz; Celeda, Malgorzata; Linden, Anthony; Heimgartner, Heinz (2016). Synthesis of hetaryl-substituted 1,2,4-trithiolanes via a three-component reaction with dihetaryl thioketones, benzyl azide, and 2,2,4,4-tetramethyl-3-thioxocyclobutanone. Journal of Sulfur Chemistry, 37(1):14-22.

Abstract

The three-component reactions with a hetaryl thioketone, 2,2,4,4-tetramethyl-3-thioxocyclobutanone, and excess benzyl azide performed at 60°C in the presence of LiClO4 lead to the formation of two types of 1,2,4-trithiolanes. As the major products, the non-symmetrical dihetaryl-substituted spiro-1,2,4- trithiolanes are formed. In addition, the symmetrical dispiro-1,2,4-trithiolane is identified. These products are formed in competitive [3 + 2] cycloadditions of the in-situ-generated thiocarbonyl S-sulfide with the thioketones used in the reaction.

The three-component reactions with a hetaryl thioketone, 2,2,4,4-tetramethyl-3-thioxocyclobutanone, and excess benzyl azide performed at 60°C in the presence of LiClO4 lead to the formation of two types of 1,2,4-trithiolanes. As the major products, the non-symmetrical dihetaryl-substituted spiro-1,2,4- trithiolanes are formed. In addition, the symmetrical dispiro-1,2,4-trithiolane is identified. These products are formed in competitive [3 + 2] cycloadditions of the in-situ-generated thiocarbonyl S-sulfide with the thioketones used in the reaction.

Altmetrics

Downloads

8 downloads since deposited on 15 Oct 2015
6 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:February 2016
Deposited On:15 Oct 2015 14:37
Last Modified:13 Sep 2016 00:00
Publisher:Taylor & Francis
ISSN:1741-5993
Funders:National Science Center (Cracow, Poland)
Additional Information:This is an Accepted Manuscript of an article published by Taylor & Francis in Journal of Sulfur Chemistry on September 12, 2015, available online: http://wwww.tandfonline.com/10.1080/17415993.2015.1082182
Publisher DOI:https://doi.org/10.1080/17415993.2015.1082182
Permanent URL: https://doi.org/10.5167/uzh-113422

Download

[img]
Preview
Content: Accepted Version
Filetype: PDF
Size: 190kB
View at publisher
[img]
Filetype: PDF - Registered users only
Size: 1MB

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations