Mechanistic Insight into the Thermal Ring Opening of the Dewar Isomer of 1,2-Dihydro-1,2-azaborinines.

ABSTRACT: In contrast to the multichannel photochemistry of benzene, 1,2-dihydro-1,2-azaborinines generally undergo a selective electrocyclic ring-closure reaction, yielding the corresponding Dewar (2-aza-3-borabicyclo[2.2.0]-hex-5-ene) isomers. The Dewar isomers react back to the dihydroazaborinines in unimolecular reactions with long half-lives at room temperature, making this isomer pair of relevance as a molecular solar thermal (MOST) energy storage system. A systematic investigation of the influence of C-backbone functionalization on the photoisomerization or the thermal ring opening has not yet been conducted. We report here a study of the late-stage C3 functionalization of 1,2-dihydroazaborinines by cross-coupling and discuss the electronic impact of aryl substitution at C3 on the properties

SUBMITTER: Biebl SM 

PROVIDER: S-EPMC12569699 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature