1975
DOI: 10.1021/jo00914a008
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Ion radicals. XXXV. Reactions of thianthrene and phenoxathiin cation radicals with ketones. Formation and reactions of .beta.-ketosulfonium perchlorates and ylides

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Cited by 34 publications
(12 citation statements)
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“…-Keto sulfones 3a-e were synthesized by the reaction of 2-bromo-1-arylethanone 1a-e with the appropriate sodium arylsulfinate 2a, b according to the reported method [10][11][12][13][14][15]. Treatment of -keto sulfones 3a-e with sodium nitrite, in acetic acid containing sulfuric acid, afforded the corresponding carboxylic acids 12a-e in addition to formic acid (14) and benzene/4-toluenesulfinic acid 15a, b (Figure 1).…”
Section: Resultsmentioning
confidence: 99%
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“…-Keto sulfones 3a-e were synthesized by the reaction of 2-bromo-1-arylethanone 1a-e with the appropriate sodium arylsulfinate 2a, b according to the reported method [10][11][12][13][14][15]. Treatment of -keto sulfones 3a-e with sodium nitrite, in acetic acid containing sulfuric acid, afforded the corresponding carboxylic acids 12a-e in addition to formic acid (14) and benzene/4-toluenesulfinic acid 15a, b (Figure 1).…”
Section: Resultsmentioning
confidence: 99%
“…Ethanones 3a-f. These compounds were prepared according to the reported method [10][11][12][13][14][15].…”
Section: Synthesis Of 1-aryl-2-arylsulfonylmentioning
confidence: 99%
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“…The resulting residue was chromatographed on silica gel column eluting with AcOEt: n-hexane (1:1) to give 3a, mp 69-70°C (lit. 12…”
Section: -Phenyl-2-thiocynanatoethanone (3a); Typical Proceduresmentioning
confidence: 99%
“…About 30 years ago, one of us reported that reactions of thianthrene-(Th •+ ), phenoxathiin-, N-methylphenothiazine-, and N-phenylphenothiazine cation radical perchlorates with ketones gave β-ketosulfonium salts 1-4 ( Figure 1) (1)(2)(3)(4). The reactions were described as probably beginning with the addition of the cation radical to the enolic form of the ketone (3), which has been supported in later work by Wayner (5).…”
Section: Introductionmentioning
confidence: 99%