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Snyder, S. A.: 2016 Science of Synthesis, 2015/4a: Applications of Domino Transformations in Organic Synthesis 1 DOI: 10.1055/sos-SD-219-00096
Applications of Domino Transformations in Organic Synthesis 1

1.4.1 Peroxy Radical Additions

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Book

Editor: Snyder, S. A.

Authors: Adu-Ampratwum, D.; Anderson, E.; Armbrust, K. W.; Devery, J.; Douglas, J.; Doyle, M. P.; Engle, K. M.; Forsyth, C. J.; Gille, F.; Halkina, T.; Hu, X.; Jamison, T.; Kelley, E. H.; Kirschning, A.; Lee, D.; Maimone, T.; Merino, E.; Nevado Blazquez, C.; O'Connor, M. J.; Ohshima, T.; Parker, K.; Renata, H.; Salvador, A.; Schaumann, E.; Shenvi, R.; Shi, L.-L.; Sittihan, S.; Snyder, S. A.; Stephenson, C. R. J.; Tang, M.; Truong, P.; Tu, Y.-Q.; Wan, K.; Wang, S.-H.; Wolling, M.; Xu, X.; Yang, Z.

Title: Applications of Domino Transformations in Organic Synthesis 1

Print ISBN: 9783131731319; Online ISBN: 9783132402522; Book DOI: 10.1055/b-003-128286

1st edition © 2016. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

In this chapter, radical addition reactions involving peroxy radical intermediates are reviewed. These transformations typically generate a carbon radical intermediate which then reacts with molecular oxygen forming a peroxy radical species. Following peroxy radical cyclization, various endoperoxide rings are constructed. Two major classes of reactions are discussed: (1) radical additions to alkenes and quenching with molecular oxygen, and (2) radical formation from the opening of cyclopropanes and incorporation of molecular oxygen. Various methods for radical initiation that are compatible with the presence of molecular oxygen are described.

Key words

peroxide synthesis - endoperoxides - cyclic peroxides - radical addition - peroxy radicals - thiyl radicals - hydroperoxidation - cyclopropane cleavage - 1,2-dioxolanes - 1,2-dioxanes - 1,2-dioxepanes
 
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