117040-43-4Relevant articles and documents
Thermal rearrangement of phenyl-substituted ketene ethylene acetals
Oda, Mitsunori,Morimoto, Kazuo,Thanh, Nguyen Chung,Ohta, Reina,Kuroda, Shigeyasu
, p. 1673 - 1680 (2003)
Thermal rearrangement of mono-, di-, and triphenyl-substituted ketene ethylene acetals was studied. Pyrolysis of all of these acetals provided phenyl-substituted tetrahydro-2-furanones as a major product. The more phenyl groups substitute on the ketene acetal skeleton, the lower reaction temperature was required for the rearrangement. In the cases of the diphenylketene acetals at high temperatures, fragmentation products, such as fluorene and benzophenone, probably derived from dipheylcarbene via diphenylketene, were observed.
Diastereoselective Synthesis of γ-Lactones through Reaction of Sulfoxonium Ylides, Aldehydes, and Ketenes: Substrate Scope and Mechanistic Studies
Peraino, Nicholas J.,Mondal, Mukulesh,Ho, Han-Jen,Beuque, Antoine,Viola, Evan,Gary, Melanie,Wheeler, Kraig A.,Kerrigan, Nessan J.
, p. 151 - 160 (2020/12/11)
In this article, we describe the synthesis of γ-lactones through the reaction of sulfoxonium ylides, aldehydes, and disubstituted ketenes. The one-pot sequential method provides access to γ-lactones from disubstituted ketenes, in moderate to excellent yields, and with good diastereoselectivity favoring the trans-diastereomer (dr up to 92 : 8). The reaction mechanism was investigated by performing labeling, crossover, and various control experiments. The results of those experiments support the reaction mechanism involving betaine formation, reaction of the betaine with a ketene to form an enolate intermediate, [3,3]-sigmatropic rearrangement of an enolate intermediate, and finally, 5-exo-tet cyclization to afford the γ-lactone product.
