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- Title
π-Insertion Reactions of Benzynes into P=N and P=S Double Bonds.
- Authors
Lopez‐Leonardo, Carmen; Raja, Rosalia; López‐Ortiz, Fernando; Ángel del Águila‐Sánchez, Miguel; Alajarin, Mateo
- Abstract
The π-insertion reactions of in situ generated benzynes into the P=N bonds of N-benzyl and N-aryl iminophosphoranes and the P=S bonds of phosphane sulfides have been examined by using the Kobayashi benzyne precursors, (2-trimethylsilyl)phenyl triflates. The reactions with iminophosphoranes afforded (2-aminophenyl)phosphonium triflates under mild conditions, most probably by a [2+2]/retro [2+2] cycloaddition sequence and further N-protonation by the solvent (CH3CN) or N-phenylation by a second molecule of benzyne. The final products of the analogous reactions with P-OCH3-substituted iminophosphoranes were the respective (2-aminophenyl)phosphane oxides, as result of a final O-demethylation event of the putative phosphonium triflate. The reactions with phosphane sulfides involve a final S-phenylation step to yield (2-phenylthio)phenylphosphonium salts.
- Subjects
BENZYNES; PHOSPHAZENES; PHOSPHINES; SULFIDES; TRIFLATE compounds; DOUBLE bonds
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 5, p1084
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301481