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Imidyl radicals. 3. Stereoselectivity of radical additions of N-haloimides to cyclic alkenes

✍ Scribed by André Kirsch; Ulrich Lüning; Oliver Krüger

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
66 KB
Volume
341
Category
Article
ISSN
1615-4150

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✦ Synopsis

N-Haloimides (1 -5) are used in two types of radical chain reactions: (i) the selective Ziegler bromination of allylic and benzylic positions [1], which are bromine atom chain reactions [2] and (ii) imidyl radical [3, 4] chain reactions like substitutions and especially additions to double bonds [5,6,7] (see scheme 1).

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Radical Addition of N-Bromophthalimide t
Radical Addition of N-Bromophthalimide to Linear and Cyclic Alkynes
✍ Uta Wille; Oliver Krüger; André Kirsch; Ulrich Lüning 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 282 KB 👁 2 views

Addition of N-bromophthalimide (1) to alkynes 3 via can be explained by the Curtin-Hammett principle. When this free-radical addition is applied to the medium-sized phthalimidyl radicals 2 introduces a bromine atom and an imidyl moiety to vicinal C atoms, and highly functionalized cycloalkyne 8, the