17396-38-2

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 1813, 1948 DOI: 10.1021/ja01185a048

Upstream product

• 1003-41-4 4H-thiopyran-4-one 
• 127-09-3 sodium acetate 
• 67-64-1 acetone 
• 408314-20-5 3,5-dibromo-1,1-dioxo-tetrahydro-1λ⁶-thiopyran-4-one 
• 57321-26-3 2,3-dihydro-4H-thiin-4-one 1,1-dioxide 
• 17396-35-9 1,1-dioxotetrahydrothiopyran-4-one 
• 57242-69-0 2,3-dihydro-4H-thiopyran-4-one 
• 162467-21-2 3-Bromo-2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxide 
• 4160-61-6 3-methoxycarbonyltetrahydropyran-4-one 
• 1072-72-6 Tetrahydrothiopyran-4-one 
• 1120-94-1 thiopyran-4-thione 
• 4131-74-2 Dimethyl 3,3'-thiodipropionate 

Downstream Products

• 17396-35-9 1,1-dioxotetrahydrothiopyran-4-one 

Relevant academic research and scientific papers

Syntheses of 4H-thiopyran-4-one 1,1-dioxides as precursors to sulfone-containing analogues of tetracyanoquinodimethane

Synthetic routes to the unsubstituted 4H-thiopynan-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation of 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.

Solid- and Solution-state Carbon-13 Nuclear Magnetic Resonance Studies of a Series of Sulphur-containing Heterocycles

Thiin-4-one (3a) and 3-methoxycarbonylthiin-4-one (7a) together with their dihydro- and tetrahydro-analogues and a number of the corresponding sulphoxides and sulphones have been studied using solution- and solid-state 13C n.m.r.These investigations highlight the usefulness of solid-state 13C n.m.r. spectroscopy for the study of keto-enol tautomerism in β-keto esters and provide new information concerning the aromaticity of thiin-4-ones.