Acylation Mechanisms of DMSO/[D6] DMSO with Di??tert??butylketene and Its Congeners
R Knorr
Index: Knorr, Rudolf European Journal of Organic Chemistry, 2011 , # 31 p. 6335 - 6342
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Citation Number: 2
Abstract
Abstract Dimethyl sulfoxide (DMSO) and tBu 2 C= C= O in diglyme require heating to about 150 C to furnish the Pummerer-type product tBu 2 CHCO 2 CH 2 SCH 3 through a novel mechanistic variant. The “ester enolate” tBu 2 C= C (O–)–O–S+(CH 3) 2 arising through the reversible addition of DMSO (step 1) to C-1 of tBu 2 C= C= O must be trapped through protonation (step 2) at C-2 by a carboxylic acid catalyst to form tBu 2 CH–C (= O)–O–S+( ...
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