ISBN 9783843931410

978-3-8439-3141-0, Reihe Organische Chemie

Rebekka Anna Bohmann
Selective Transformations of Sulfondiimines

162 Seiten, Dissertation Rheinisch-Westfälische Technische Hochschule Aachen (2017), Softcover, A5

Zusammenfassung / Abstract

In spite of their intriguing properties and promising biological activities, to date, the di-aza analogs of sulfones, namely sulfondiimines, represent a highly underrated class of compounds. As a contribution to overcome the existing limitations in their syntheses and applications, this thesis focused on the variable structural modifications of sulfondiimine derivatives by the development of methods for their N-arylations, N-alkenylations, N-alkylations, and alpha-functionalizations, and their applications in the syntheses of 1,2-(benzo)thiazines.

Thereby, the abilities of sulfondiimines for different applications in transition-metal-catalyzed or -free synthetic methods, with “superbasic” media, as directing groups in C‒H-bond functionalizations, or as organolithium reagents have been demonstrated. In addition, paying particular attention to potential pharmacological and agricultural agents, a library of structurally diverse sulfondiimine-based products was created.

On the basis of these findings, the utility of the sulfondiimine compound class should be re-evaluated, and their derivatives are recommended as reasonable alternatives to well-established structurally related molecular scaffolds such as sulfones and sulfoximines for future applications.