The Eschenmoser sulfide contraction is an organic reaction first described by Albert Eschenmoser for the synthesis of 1,3-dicarbonyl compounds from a thioester.[1][2][3] The method requires a base and a tertiary phosphine. The method is of some relevance to organic chemistry and has been notably applied in the vitamin B12 total synthesis.
A base abstracts the labile hydrogen atom in the thioester, a sulfide anion is formed through an episulfide intermediate which is removed by the phosphine.[4]
- ^ Organic syntheses based on name reactions, Volume 22 2002 Alfred Hassner,C. Stumer
- ^ A New Type of Corrin Synthesis Angewandte Chemie International Edition in English Volume 8, Issue 5, Date: May 1969, Pages: 343-348 Yasuji Yamada, D. Miljkovic, P. Wehrli, B. Golding, P. Löliger, R. Keese, K. Müller, A. Eschenmoser doi:10.1002/anie.196903431
- ^ Sulfidkontraktion via alkylative Kupplung: Eine methode zur darstellung von -dicarbonylderivaten. Über synthetische methoden, 1. Mitteilung Helvetica Chimica Acta Volume 54, Issue 2, Date: 1971, Pages: 710-734 M. Roth, P. Dubs, E. Götschi, A. Eschenmoser doi:10.1002/hlca.19710540229
- ^ Loeliger, P.; Flückiger, E. (1976). "Sulfide Contraction via Alkylative Coupling: 3-Methyl-2,4-Hepthanedione". Organic Syntheses. 55: 127. doi:10.15227/orgsyn.055.0127.