Related Experiment Video
Updated: Feb 6, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Revisiting Arene C(sp2 )-H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a
Yeongyu Hwang1,2, Yoonsu Park1,2, Yeong Bum Kim1,2
1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141, Republic of Korea.
Abstract:
Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C-H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed.
Related Concept Videos
Intermolecular vs Intramolecular Forces
The Evidence for Evolution
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Intramolecular Aldol Reaction
Radical Reactivity: Intramolecular vs Intermolecular
C4 Pathway and CAM
C4 Pathway
The C4 pathway is used by plants such as...

