Preparation and Diels-Alder Reactions of 1,1-Dicarbonylalkenes

Thomas R Hoye, Andrew J. Caruso, Andrew S. Magee

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1,1-Dicarbonyl- (ester, ketone, lactone) substituted alkenes are prepared from the corresponding saturated 1-phenylsulfinyl derivatives. These are formed from precursor sulfides, which can be efficiently prepared either by oxidation of β-hydroxy-α-phenylsulfenylcarbonyl compounds or direct acylation of α-phenylsulfenyl enolate anions with acid chlorides. Some of the title compounds can be isolated and then reacted while others are generated and reacted in situ in a Diels-Alder fashion with cyclopentadiene. Endo-exo selectivities are discussed.

Original languageEnglish (US)
Pages (from-to)4152-4156
Number of pages5
JournalJournal of Organic Chemistry
Issue number21
StatePublished - Jan 1 1982


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