Abstract
Abstract 14β-Cholorocodeine1 reacted with phthalimide under the conditions of the Mitsunobu reaction (with TPP and DEAD or DIAD ) to give the expected phthalimide derivative3 together with 6β, 14β-dichloro-6-deoxycodeine4 and the diene6 or7. 14β-Bromocodeine2 reacted similarly but did not give any phthalimido derivative. The mechanism of these consecutive reactions has been investigated. With diphenylphosphoryl azide 6β-azido-14β-chloro15 and 6β-azido-14β-bromo16 derivatives were obtained.
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