UZH-Logo

Maintenance Infos

Synthesis of Five-Membered Sulfur-Heterocycles via 1,5-Dipolar Electrocyclization of Thiocarbonyl Ylides and Related Processes


Mloston, G; Heimgartner, H (2011). Synthesis of Five-Membered Sulfur-Heterocycles via 1,5-Dipolar Electrocyclization of Thiocarbonyl Ylides and Related Processes. Current Organic Chemistry, 15(5):675-693.

Abstract

The reactive thiocarbonyl ylides belong to the less well-known class of the so-called ‘sulfur-centered 1,3-dipoles’. Only in recent years have the [2+3] cycloadditions with thiocarbonyl ylides been extensively explored, mainly as a useful method for the synthesis of three- and five-membered sulfur heterocycles. The goal of the present review is to demonstrate the potential of the 1,5-dipolar electrocyclization of properly substituted thiocarbonyl ylides as an alternative approach to syntheses of sulfur heterocycles such as 1,3-oxathiolanes, 1,3-thiazoles, 1,3-dithioles, and thiophenes. Thermal, as well as metal-catalyzed, generations of the reactive intermediates from diazo and thiocarbonyl precursors are summarized and discussed. The presented examples show the scope and limitations of this general but relatively scarcely-investigated reaction.

The reactive thiocarbonyl ylides belong to the less well-known class of the so-called ‘sulfur-centered 1,3-dipoles’. Only in recent years have the [2+3] cycloadditions with thiocarbonyl ylides been extensively explored, mainly as a useful method for the synthesis of three- and five-membered sulfur heterocycles. The goal of the present review is to demonstrate the potential of the 1,5-dipolar electrocyclization of properly substituted thiocarbonyl ylides as an alternative approach to syntheses of sulfur heterocycles such as 1,3-oxathiolanes, 1,3-thiazoles, 1,3-dithioles, and thiophenes. Thermal, as well as metal-catalyzed, generations of the reactive intermediates from diazo and thiocarbonyl precursors are summarized and discussed. The presented examples show the scope and limitations of this general but relatively scarcely-investigated reaction.

Citations

10 citations in Web of Science®
10 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

3 downloads since deposited on 10 Feb 2011
0 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2011
Deposited On:10 Feb 2011 16:32
Last Modified:05 Apr 2016 14:45
Publisher:Bentham Science
ISSN:1385-2728
Publisher DOI:https://doi.org/10.2174/138527211794518961
Permanent URL: https://doi.org/10.5167/uzh-45188

Download

[img]
Filetype: PDF - Registered users only
Size: 507kB
View at publisher

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