Abstract
Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified using C-13-labelling and led to a revised mechanism featuring two distinct skeletal rearrangements. The mechanistic proposal has been rationalised against the reaction of a range of C-13- and deuterium-labelled substrates.
Original language | English |
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Pages (from-to) | 839-846 |
Number of pages | 8 |
Journal | Beilstein Journal of Organic Chemistry |
Volume | 7 |
DOIs | |
Publication status | Published - 1 Jun 2011 |
Keywords
- isotopic labelling
- cycloisomerisation
- skeletal rearrangement
- pyrrole
- gold
- 1,2-aryl shift