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Sulfur Ylides (Update 2014)


Mloston, Grzegorz; Heimgartner, Heinz (2014). Sulfur Ylides (Update 2014). In: Brondsted Nielsen, M; Krause, N; Marek, I; Schaumann, E; Wirth, T. Science of Synthesis Knowledge Updates: 2014/2. Stuttgart: Thieme Verlag, 377-392.

Abstract

The mansucript is an update to the earlier Science of Synthesis contribution describing methods for the in situ generation of thiocarbonyl ylides and Corey-Chaykovski reagents (sulfonium and sulfoxonium methanides). Whereas thiocarbonyl ylides react as electron rich 1,3-dipoles, Corey-Chaykovski reagents act as methylidene transferring agents. The most relevant application of thiocarbonyl ylides relates to the synthesis of tetrahydrothiophene (thiolane) and 1,3-dithiolane derivatives via [3+2] cycloadditions with electron deficient C,C and C=S dipolarophiles, respectively. In the recent decade, Corey-Chaykovsky reagents were widely applied for cyclopropanation, epoxidation, aziridination as well as for diverse heterocyclization reactions. In all cases, asymmetric versions of the applied protocols is of great interest.

Abstract

The mansucript is an update to the earlier Science of Synthesis contribution describing methods for the in situ generation of thiocarbonyl ylides and Corey-Chaykovski reagents (sulfonium and sulfoxonium methanides). Whereas thiocarbonyl ylides react as electron rich 1,3-dipoles, Corey-Chaykovski reagents act as methylidene transferring agents. The most relevant application of thiocarbonyl ylides relates to the synthesis of tetrahydrothiophene (thiolane) and 1,3-dithiolane derivatives via [3+2] cycloadditions with electron deficient C,C and C=S dipolarophiles, respectively. In the recent decade, Corey-Chaykovsky reagents were widely applied for cyclopropanation, epoxidation, aziridination as well as for diverse heterocyclization reactions. In all cases, asymmetric versions of the applied protocols is of great interest.

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Additional indexing

Item Type:Book Section, not refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2014
Deposited On:10 Jun 2014 12:39
Last Modified:22 Nov 2017 17:00
Publisher:Thieme Verlag
ISBN:978-3-1317-6261-0
Related URLs:https://www.thieme.de/shop/Houben-Weyl--SoS/Science-of-Synthesis-Knowledge-Updates-9783131762610/p/000000000283414401

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