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- W2949528094 abstract "Benzothiet-2-one (5) is obtained as a neat solid, stable below -20 °C (-45 °C in solution), by flash vacuum pyrolysis of benzothiophene-2,3-dione (9). Naphtho[2,3-b]thiet-2-one (21) and naphtho[2,l-b]thiet-l-one (42) are obtained as stable crystalline solids in near-quantitative yields from the corresponding napthothiophenediones 20 and 41. Naphtho[2,3-b]oxet-2-one (31) and naphtho[2,3-b]azetin-2-one (36) were generated and observed by IR spectroscopy to be stable below -40 °C and 0 °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. Naphtho[2,l-b]thiet-l-one (42) reacts with 1-thiocarbonyl-lH-indene (45) to give cycloaddition product 46. Naphthothietones 21 and 42 react with dicyclohexylcarbodiimide to furnish 2-imino-l,3-thiazin-4-one derivatives 47 and 49." @default.
- W2949528094 created "2019-06-27" @default.
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- W2949528094 date "1988-02-09" @default.
- W2949528094 modified "2023-09-25" @default.
- W2949528094 title "ChemInform Abstract: Benzothiet-2-ones: Synthesis, Reactions, and Comparison with Benzoxet- 2-ones and Benzazetin-2-ones." @default.
- W2949528094 cites W1976528344 @default.
- W2949528094 doi "https://doi.org/10.1002/chin.198806133" @default.
- W2949528094 hasPublicationYear "1988" @default.
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