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Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines.

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 (13)C-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 (13)C- and deuterium-labelled substrates.

SUBMITTER: Davies PW

PROVIDER: S-EPMC3135223 | biostudies-other | 2011

REPOSITORIES: biostudies-other

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Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines.

Davies Paul W PW Martin Nicolas N Spencer Neil N

Beilstein journal of organic chemistry 20110621

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 (13)C-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 (13)C- and deuterium-labelled substrates. ...[more]

PMID: 21804880

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