24322-10-9Relevant academic research and scientific papers
Deazetation of 1,4-Dimethyl-2,3-diazabicyclooct-2-ene: Stereochemistry and the Formation of Dimethylcyclohexene
Edmunds, Andrew J. F.,Samuel, Christopher J.
, p. 457 - 460 (2007/10/02)
Irradiation of stereospecifically labelled 2H2>-1,4-dimethyl-2,3-diazabicyclooct-2-ene gave 1,4-dimethylbicyclohexane and 2,5-dimethylhexa-1,5-diene with the label randomly distributed between the stereochemically differentiated positions, together with 1,4-dimethylcyclohexene, which was only formed in the direct photolysis.
Photolysis of Reluctant Azoalkanes. Effect of Structure on Photochemical Loss of Nitrogen from 2,3-Diazabicyclooct-2-ene Derivatives
Engel, Paul S.,Horsey, Douglas W.,Keys, Dalen E.,Nalepa, Christopher J.,Soltero, Luis R.
, p. 7108 - 7114 (2007/10/02)
Azoalkanes containing the bicycloskeleton often prove to be remarkable stable toward loss of nitrogen.These derivatives of 2,3-diazabicyclooct-2-ene (DBO) also exhibit fluorescence whose lifetime extends to 600 ns.This paper is an attempt to understand the effect of fused rings and bridgehead substituents on the photochemical and photophysical properties of DBO.The main factor controlling quantum yields of nitrogen is a 6-11 kcal mol-1 activation barrier that differs for the singlet and triplet states and that seems to mimic the barrier to ground-state deazatization.The product distribution for DBO derivatives is rationalized on the basis of interconverting singlet 1,4-biradicaloids.
