The mechanism of the gold(I)-catalyzed Meyer-Schuster rearrangement of 1-phenyl-2-propyn-1-ol 4- cyclization.

Dalton Trans

Department of Chemistry, Biology and Biotechnology, University of Perugia, Via Elce di Sotto 8, I-06123, Perugia, Italy. and Institute of Chemical Sciences and Technologies "Giulio Natta" of CNR (CNR-SCITEC), c/o Department of Chemistry, Biology and Biotechnology, University of Perugia, Via Elce di Sotto 8, I-06123, Perugia, Italy.

Published: April 2021

With the aim of rationalizing the experimental counterion- and solvent-dependent reactivity in the gold(i)-catalyzed Meyer-Schuster rearrangement of 1-phenyl-2-propyn-1-ol, a computational mechanistic study unraveled the unexpected formation of a gold-oxetene intermediate via commonly unfavorable 4-endo-dig cyclization triggered by the counterion in low polarity solvents.

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Source
http://dx.doi.org/10.1039/d1dt00080bDOI Listing

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