Dienophilic thioaldehydes and dithioesters formed by base-catalysed cleavage of alkyl phthalimidosulfanylacetates

GW Kirby, AW Lochead, S Williamson

Index: Kirby, Gordon W.; Lochead, Alistair W.; Williamson, Sharon Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 10 p. 977 - 984

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Abstract

Treatment of ethyl and methyl phthalimidosulfanylacetate 1a and 1b with triethylamine at room temperature generates [eqn.(1)] the transient thioaldehydes, ethyl and methyl thioxoacetate 2, which have been trapped in situ with 2, 3-dimethylbuta-1, 3-diene to yield the Diels–Alder cycloadducts 8a and 8b in high yield. The cycloadducts 9, 10 and 11a and 12a of ethyl thioxoacetate 2a and anthracene, cyclohexa-1, 3-diene and cyclopentadiene, ...