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- Title
Synthesis and Reactions of Homoditopic Stable Nitrile N‐Oxide as a Powerful Tool for Catalyst‐Free Constructions of Macromolecular Architectures.
- Authors
Ooba, Souma; Nakajima, Noriyuki; Hamada, Masahiro; Takata, Toshikazu; Koyama, Yasuhito
- Abstract
Nitrile N‐oxide is a highly reactive 1,3‐dipole that undergoes 1,3‐dipolar cycloaddition reactions to various dipolarophiles. However, the high reactivity of nitrile N‐oxide leads to side reactions with nucleophiles and self‐reactions, resulting in a decrease in the cycloadduct yield. The bulky substituent around nitrile N‐oxide kinetically suppresses such undesirable side reactions, stabilizing nitrile N‐oxide, and improving 1,3‐dipolar cycloaddition efficiency. Homoditopic stable nitrile N‐oxides as a ligation tool between unsaturated bonds are developed, although the challenge of the large‐scale synthesis remains. Herein, the practical synthesis of a homoditopic stable nitrile N‐oxide from bismaleimide is reported. Three simple steps, namely, Michael addition, oximation, and oxidation, produce the homoditopic nitrile N‐oxide in 87% overall yield without purification process using column chromatography. The ligation capacity of nitrile N‐oxide is discussed through polycycloadditions with several bisdipolarophiles and the cross‐linking reaction of polyacrylonitrile.
- Subjects
NITRILE oxides; COLUMN chromatography; RING formation (Chemistry); NUCLEOPHILES; OXIDATION
- Publication
Macromolecular Chemistry & Physics, 2022, Vol 223, Issue 20, p1
- ISSN
1022-1352
- Publication type
Article
- DOI
10.1002/macp.202200183