Mechanisms of the Intriguing Rearrangements of Activated Organic Species [article]

David Grant Harman, University, The Australian National, University, The Australian National
2008
The β-acyloxyalkyl radical rearrangement has been known since 1967 but its mechanism is still not fully understood, despite considerable investigation. Since the migration of a β-trifluoroacetoxy group generally proceeds more rapidly and with more varied regiochemistry than its less electronegative counterparts, this reaction was studied in the hope of understanding more about the subtleties of the mechanism of the β- acyloxyalkyl radical rearrangement. The mechanism of the catalysed
more » ... nt of Nalkoxy- 2(1H)-pyridinethiones was also explored because preliminary studies indicated that the transition state (TS) for this process was isoelectronic with TSs postulated for the β-acyloxyalkyl radical and other novel rearrangements. ¶ ...
doi:10.25911/5d7a29ed7c4e9 fatcat:uuqn7en2nrcu7cmpe7a5t3wovy