Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 42, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202211800
Keywords
Aluminyl Anion; Bond Cleavage; C-H Activation; Diazirine; pi Bonding
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Funding
- Nanyang Technological University (NTU)
- Singapore Ministry of Education [MOE-T2EP10220-0002]
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The [1+2] cycloaddition reaction between a cyclic (alkyl)-(amino)aluminyl anion and diaryldiazomethane results in the formation of an AlN2 three-membered ring species, which shows interesting reactivity and properties.
[1+2] cycloaddition between a cyclic (alkyl)-(amino)aluminyl anion (3) and diaryldiazomethane affords an AlN2 three-membered ring species (4). Compound (4) is thermally unstable and spontaneously releases N-2 gas under the mild reaction condition to generate an ion-separated species 5. An X-ray study shows that the anionic part of 5 bears a considerable short exocyclic Al-C bond, and computational studies involving molecular orbital and natural bond orbital analysis indicate the A1=C pi bonding character. The Al=C moiety of 5 undergoes intramolecular C-H activation. Moreover, reaction of 5 with a diazo compound leads to the reduction and complete cleavage of the N=N double bond.
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