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. Author manuscript; available in PMC: 2016 May 27.
Published in final edited form as: J Am Chem Soc. 2015 Mar 5;137(10):3600–3609. doi: 10.1021/jacs.5b00022

Scheme 3. Structure-Reactivity Relationships Across a Family of Thiono-Claisen Rearrangements.

Scheme 3

a Synthetic schemes and measured half-times for the four thiono-Claisen rearrangements studied here. b 19F NMR stack plot for the rearrangement of the pentafluorophenyl thionocarbonate ester @ RT. Note: The t = 0 point is arbitrarily labeled; this rearrangements proceeds too fast to capture a true starting time point.