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Transforming benzylideneamine N,C-chelate boron compounds to BN-cycloocta-/cyclohepta-trienes bearing a tetrasubstituted B[double bond, length as m-dash]N unit via photoisomerization.

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A series of benzylideneamine N,C-chelate boron compounds have been found to undergo rapid multistructural transformations with UV irradiation, yielding new BN-cycloocta-1,3,6-triene ((4Z,6Z)-1,2,3,8-tetrahydro-1,2-azaborocine) and BN-cyclohepta-1,3,5-triene (2,7-dihydro-1H-1,2-azaborepine) derivatives with a tetrasubstituted B[double… Click to show full abstract

A series of benzylideneamine N,C-chelate boron compounds have been found to undergo rapid multistructural transformations with UV irradiation, yielding new BN-cycloocta-1,3,6-triene ((4Z,6Z)-1,2,3,8-tetrahydro-1,2-azaborocine) and BN-cyclohepta-1,3,5-triene (2,7-dihydro-1H-1,2-azaborepine) derivatives with a tetrasubstituted B[double bond, length as m-dash]N unit quantitatively. The simple imine donor also lends itself to achieving photoreactivity in compounds with two phenyl substituents on boron, which is the first example for this type of organoboron photochemistry.

Keywords: boron compounds; benzylideneamine chelate; tetrasubstituted double; bond length; chelate boron; double bond

Journal Title: Chemical communications
Year Published: 2018

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