New reagents for electrophilic modification of olefins
By: by Larissa Krasnova.
Contributors: University of Toronto.  Dept. Of Chemistry.
Published: 2006
Language: eng
Number of pages: 255
ISBN-13: 9780494157510
Description: The new methodology was further applied towards the synthesis of alpha-bromoaziridines. Synthesis and chemical reactivity of alpha-bromoaziridines are described in Chapter 2. In addition, particular attention was paid to the rearrangement of alpha-bromoaziridines into the corresponding alpha-bromohydrazones and their chemical reactivity.A new reagent for olefin aziridination has been developed. The reaction scope of aziridination and sulfoximination with N-aminophthalimide and diacetoxyiodobenzene was studied and the results are summarized in Chapter 1. The main advantages of the developed procedure are high yields, tolerance towards functional groups and straightforward scale-up.Chapter 3 describes new reactivity of the sulfinyl amides and their application as reagents for the modification of the double bonds. Reaction between alkenes and sulfinyl amides in the presence of POCl3 was found to proceed with the formation of beta-chlorosulfides or beta-hydroxysulfides. Optimized reaction conditions were applied to a range of substrates. This chemistry provides a good alternative to the currently used methods of sulfides syntheses.
Notes: Source: Dissertation Abstracts International, Volume: 67-06, Section: B, page: 3139.

Advisor: Andrei K. Yudin

Thesis (Ph.D.)--University of Toronto, 2006.

Includes bibliographic references.

Electronic version licensed for access by U. of T. users.