Thermal cycloreversion of 4H-1,3-dioxine-4-thiones to acyl thioketenes:a general synthesis of β-keto thioic O-acid derivatives
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 6,p. 775-776
- https://doi.org/10.1039/cc9960000775
Abstract
Thermal cycloreversion of 4H-1,3-dioxine-4-thiones gives acyl thioketenes as reactive intermediates, trapping of which by nucleophiles provides a general synthesis for β-keto thioic O-acid derivatives.Keywords
This publication has 21 references indexed in Scilit:
- A Computational Study of the Thermal Cycloreversion of 2,2,6-Trimethyl-4H-1,3-dioxin-4-one and a Related Species: Retro-Diels-Alder Reaction or Concerted Nucleophilic Attack?The Journal of Organic Chemistry, 1995
- On the Development of Aromaticity in Cycloadditions: Ab Initio Transition Structures for the Trimerization of Acetylene and for the Addition of Ethylene and Acetylene to Formyl keteneThe Journal of Organic Chemistry, 1995
- Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. 46. 2-(l-Menthyloxycarbonyl)-2,6-dimethyl-1,3-dioxin-4-one and Related Compounds. Relationship between Facial Selectivity and PyramidalizationJournal of the American Chemical Society, 1995
- An ab Initio Study of the Reactivity of Formylketene. Pseudopericyclic Reactions RevisitedJournal of the American Chemical Society, 1994
- Substituent effects on ketene structure and stability: an ab initio studyJournal of the American Chemical Society, 1991
- Cycloaddition reactions of acyl ketenes with enol ethers: A general synthesis of 2-alkoxy-2,3-dihydro-4h-pyran-4-ones.Tetrahedron Letters, 1990
- 1,3‐dioxin‐4‐ones as versatile intermediates for organic synthesisJournal of Heterocyclic Chemistry, 1990
- A new, highly efficient, selective methodology for formation of medium-ring and macrocyclic lactones via intramolecular ketene trapping: an application to a convergent synthesis of (-)-kromycinJournal of the American Chemical Society, 1989
- Kinetic and spectroscopic studies on the thermal decomposition of 2,2,6-trimethyl-4H-1,3-dioxin-4-one. Generation of acetylketeneJournal of the American Chemical Society, 1989
- Synthesis of 1,3-dioxin-4-one derivatives.CHEMICAL & PHARMACEUTICAL BULLETIN, 1983