Canadian journal of chemistry

Intramolecular sensitization within steroids: Excited-state interaction of C-17 α and β carbon bromine bonds with a C-6 carbonyl group

WS Li, L Torun, H Morrison

Index: Li, Wen-Shan; Torun, Lokman; Morrison, Harry Canadian Journal of Chemistry, 2003 ,  vol. 81,  # 6  p. 660 - 668

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Citation Number: 4

Abstract

The synthesis, photochemistry, and photophysics of 17α-bromo-3α-(triphenylsilyloxy)-5α- androstan-6-one (1) and 17β-bromo-3β-(triphenylsilyloxy)-5α-androstan-6-one (2) have been studied in aqueous tetrahydrofuran. The 17α-bromo isomer gives evidence (reduced φf, τ1, and φisc for the ketone) for interaction between the ketone and C Br moieties in the excited singlet state. Some photodehalogenation is also observed upon excitation of the ...