Novel aspects of carbonyl oxide chemistry

✍ Scribed by Katsuya Ishiguro; Takayuki Nojima; Yasuhiko Sawaki

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 127 KB
• Volume: 10
• Category: Article
• ISSN: 0894-3230
• DOI: 10.1002/(sici)1099-1395(199711)10:11<787::aid-pca948>3.0.co;2-1

✦ Synopsis

The structural and chemical properties of 1,3-dipolar peroxidic species (X-O-O) such as ozone (X = O) and carbonyl oxides (X = R 2 C) depend significantly on the nature of X. Although cyclic O 3 is thermodynamically unstable, dioxiranes, cyclic isomers of carbonyl oxides, are isolable and have been fully characterized. In contrast to the well known electrophilic nature of ozone, carbonyl oxides usually act as a nucleophilic oxygen transfer agent, but their reactivity could be altered by substituents. It is expected that the chemistry of R 2 C-O 2 species will provide a good starting point for a better understanding of dioxygen complexes (X-O 2 ) with various Xs. Interesting aspects of carbonyl oxide chemistry are discussed, including methods of generation, cyclization to dioxiranes and the nature of their oxygen transfer activities.