We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
The Dewar Isomer of 1,2‐Dihydro‐1,2‐azaborinines: Isolation, Fragmentation, and Energy Storage.
- Authors
Edel, Klara; Yang, Xinyu; Ishibashi, Jacob S. A.; Lamm, Ashley N.; Maichle‐Mössmer, Cäcilia; Giustra, Zachary X.; Liu, Shih‐Yuan; Bettinger, Holger F.
- Abstract
Abstract: The photochemistry of 1,2‐dihydro‐1,2‐azaborinine derivatives was studied under matrix isolation conditions and in solution. Photoisomerization occurs exclusively to the Dewar valence isomers upon irradiation with UV light (>280 nm) with high quantum yield (46 %). Further photolysis with UV light (254 nm) results in the formation of cyclobutadiene and an iminoborane derivative. The thermal electrocyclic ring‐opening reaction of the Dewar valence isomer back to the 1,2‐dihydro‐1‐<italic>tert</italic>‐butyldimethylsilyl‐2‐mesityl‐1,2‐azaborinine has an activation barrier of (27.0±1.2) kcal mol−1. In the presence of the Wilkinson catalyst, the ring opening occurs rapidly and exothermically (Δ<italic>H</italic>=(−48±1) kcal mol−1) at room temperature.
- Subjects
ISOMERS; ENERGY storage; PHOTOCHEMISTRY; CHEMICAL derivatives; SOLUTION (Chemistry); PHOTOISOMERIZATION; PHOTOLYSIS (Chemistry)
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 19, p5394
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201712683