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- Title
An Aminative Rearrangement of O‐(Arenesulfonyl)hydroxylamines: Facile Access to ortho‐Sulfonyl Anilines.
- Authors
Morrill, Charlotte; Gillespie, James E.; Phipps, Robert J.
- Abstract
Ortho‐sulfonyl anilines are important building blocks for a range of applications. We report the discovery of an aromatic rearrangement reaction of O‐(arenesulfonyl)hydroxylamines which leads directly to ortho‐sulfonyl anilines through formation of a new C−N bond with excellent levels of regiocontrol for the ortho position(s) over all others. We establish that the rearrangement is proceeding through an intermolecular mechanism and propose that the regiocontrol observed is the result of attractive non‐covalent interactions occurring during the C−N bond‐forming step. Importantly, this method is complementary to classical aniline sulfonation in terms of the variously substituted regioisomers that can be obtained and it is also applicable to O‐(benzylsulfonyl) hydroxylamines.
- Subjects
ANILINE; REARRANGEMENTS (Chemistry); SULFONATION; SULFONYL compounds
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 33, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202204025