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Dimethyl sulfoxide (DMSO) and tBu2C=C=O in diglyme require heating to about 150 °C to furnish the Pummerer‐type product tBu2CHCO2CH2SCH3 through a novel mechanistic variant. The “ester enolate” tBu2C=C(O–)–O–S+(CH3)2 arising through the reversible addition of DMSO (step 1) to C‐1 of tBu2C=C=O must be trapped through protonation (step 2) at C‐2 by a carboxylic acid catalyst to form tBu2CH–C(=O)–O–S...
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