132335-19-4Relevant articles and documents
Arene Imine Derivatives of Chrysene and of Benzochrysene: 1a,11c-Dihydrochrysenoazirine and 1a,13c-Dihydrobenzochrysenoazirine
Abu-Shqara, Elias,Elg'amal, Shafea,Blum, Jochanan
, p. 1681 - 1684 (2007/10/02)
The syntheses of the K-imines (which are also benzo-bay-region derivatives) of chrysene (1) and benzochrysene (2) are described.The preparation of 1a,11c-dihydrochrysenoazirine (5) was accomplished by treatment of 1a,11c-dihydrochrysenooxirene (4) with sodium azide, and the mixture of trans-azido-alcohols 6 and 7, so formed, was either cyclized with triethyl phosphite, or converted into E-6-azido-5-chloro-5,6-dihydrochrysene (8) followed by lithium aluminium hydride reduction.The synthesis of 1a,13c-dihydrobenzochrysenoazirine (12) included the transformation of the corresponding oxide 11 into a mixture of E-9-azido-9,10-dihydrobenzochrysen-10-ol (13) and E-10-azido-9,10-dihydrobenzochrysen-9-ol (14), and reaction with tri-n-butylphosphine to give a mixture of Staudinger adducts 15 and 16 that underwent thermal decomposition into 12 upon heating in boiling dichloromethane.
