21083-36-3

Usage

InChI:InChI=1/C7H4OS/c8-7-5-3-1-2-4-6(5)9-7/h1-4H

Upstream product

• 493-57-2 benzo-[b]thiophene-2,3-dione 
• 1034249-74-5 4H-1,3-benzodithiin-4-one 

Downstream Products

• 21083-38-5 dibenzo[b,f][1,5]dithiocin-6,12-dione 
• 5459-63-2 bis[2-(methoxycarbonyl)phenyl]disulfide 
• 39264-06-7 1,9,17-trithia-[2.2.2]orthocyclophane-2,10,18-trione 
• 4892-02-8 Methyl thiosalicylate 
• 75126-75-9 (6-thioxo-2,4-cyclohexadien-1-ylidene)methanone 

Relevant academic research and scientific papers

Flash vacuum thermolysis of 4H-3,1-benzoxathiin-4-thione: UV-photoelectron spectroscopy characterization and quantum chemistry studies

The mechanism of the reaction of 4H-3,1-benzoxathiin-4-thione (3) under flash vacuum thermolysis conditions has been studied by UV-photoelectron spectra. It was shown that in the first step of the reaction at 400° 3 underwent the Schoenberg - Newman - Kwart rearrangement to give 4H-1,3-benzodithiin-4-one (6). Increasing of the temperature to 650° resulted in the elimination of thioformaldehyde and the formation of benzothiet-2-one (1). Subsequent elevation of the temperature prompted presumably the ring opening of 1 to (6-thioxocyclohexa-2,4-dien-1-ylidene) methanone (7) (at 680°), which at 700° eliminated CO and underwent a Wolff-type ring contraction to give (cyclopenta-2,4-dien-1-ylidene)methanethione (2). UV-Photoelectron spectra were recorded at different steps of the reaction and analyzed considering the theoretical evaluation of ionization potentials.

Benzothiet-2-ones: Synthesis, Reactions, and Comparison with Benzoxet-2-ones and Benzazetin-2-ones

Benzothiet-2-one (5) is obtained as a neat solid, stable below -20 deg C(-45 deg C in solution), by flash vacuum pyrolysis of benzothiophene-2,3-dione (9).Naphthothiet-2-one (21) and naphthothiet-1-one (42) are obtained as stable crystalline solids in near-quantitative yields from the corresponding naphthothiophenediones 20 and 41.Naphthooxet-2-one (31) and naphthoazetin-2-one (36) were generated and observed by IR spectroscopy to be stable below -40 deg C and 0 deg C, respectively.The thietones, oxetones, and azetinones undergo rapid ring-opening reactions with methanol to give the corresponding carboxylic acid esters.They undergo thermal CO elimination with concomitant Wolff-type ring contraction to thioketenes (17, 25, 45), ketenes (30), and nitriles (37), respectively.The di-, oligo-, and polymerization of the thietones has been elucidated.Naphthothiet-1-one (42) reacts with 1-thiocarbonyl-1H-indene (45) to give cycloaddition product 46.Naphthothietones 21 and 42 react with dicyclohexylcarbodiimide to furnish 2-imino-1,3-thiazin-4-one derivatives 47 and 49.