A BN-Benzvalene
Tomoya Ozaki, Sierra K. Bentley, Nina Rybansky, Бо Ли, Shih‐Yuan Liu
Abstract
The synthesis and crystallographic characterization of BN-benzvalene, the first second-row heteroatom-containing benzvalene, is described. BN-benzvalenes are produced via photoexcitation of C5-aryl-substituted 1,2-azaborines under flow conditions. Mechanistic studies support a boron-specific, two-step photoisomerization pathway involving a BN-Dewar benzene intermediate, which is distinct from the photoisomerization pathway proposed in benzene and phospha- and silabenzenes for the formation of their respective benzvalene analogues.
Topics & Concepts
ChemistryPhotoisomerizationPhotoexcitationBenzeneHeteroatomBenzene derivativesBoronIsomerizationArylPhotochemistryCharacterization (materials science)StereochemistryOrganic chemistryNanotechnologyChemical synthesisCatalysisExcited stateIn vitroBiochemistryNuclear physicsRing (chemistry)Materials scienceAlkylPhysicsOrganoboron and organosilicon chemistryRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions