The Journal of Organic Chemistry

Denitrogenation of bicyclic azoalkanes through photosensitized electron transfer: generation and intramolecular trapping of radical cations

W Adam, J Sendelbach

Index: Adam, Waldemar; Sendelbach, Juergen Journal of Organic Chemistry, 1993 , vol. 58, # 20 p. 5316 - 5322

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Citation Number: 22

Abstract

To elucidate the intermediates that intervene in the denitrogenation of bicyclic azoalkanes by photosensitized electron transfer (PET), the 2, 3-diazabicyclo [2.2. 11 hept-2-ene (DBH) derivative lb was synthesized, and its PET reactions were examined. With triphenylpyrylium tetrafluoroborate (TPT) or 9, lO-dicyanoanthracene (DCA) as sensitizers and biphenyl as cosensitizer, the azoalkane lb gave through intramolecular cyclization the spiro ethers 5 ...