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Radical Addition of N-Bromophthalimide to Linear and Cyclic Alkynes by Uta Wille; Oliver Krüger; André Kirsch; Ulrich Lüning is a Chemistry article available to read on EtoBox.

What is Radical Addition of N-Bromophthalimide to Linear and Cyclic Alkynes about?

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 regular addition product 9 is obtained in addition to products resulting from a transannular alkenes 5 are generated. The regioselectivity of the radical attack is controlled by steric and electronic effects, whereas cyclization. Furthermore, a parallel bromine radical chain is initiated to yield the highly brominated products 11 and 12. the stereochemistry at the newly formed C=C double bond [ ] Part 3: Ref. [4d] Scheme 1. Radical addition of N-bromophthalimide (1) to linear [a] Institut für Organische Chemie der alkynes 3 Christian-

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Author

Uta Wille; Oliver Krüger; André Kirsch; Ulrich Lüning

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 1434-193X)

Published

1999

Language

EN

Field

Chemistry (Physical Sciences)