1999
DOI: 10.1016/s0040-4039(99)00213-0
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α-Chlorination of ketones using p-toluenesulfonyl chloride

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Cited by 63 publications
(26 citation statements)
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“…7, 149.9, 133.3, 128.8, 127.2, 124.7, 124.5, 61.0, 24 = 7.8,1.5 Hz,1H),1H),2H),3.90 (s,3H);13 C NMR (75 MHz,CDCl3) δ 155.0,130.3,127.8,122.4,121.3,112.1, 4-Chloroanisole (10c): 7.19 (dd,J = 8.8,2.4 Hz,1H),6.85 (d,J = 8.8 Hz,1H),3.89 (s,3H); 13 C NMR (50 MHz, CDCl 3 ) δ 152. 2,128.3,125.9,123.9,121.6,111.1,54.7;MS (EI) ), 201,199,197 (100),195,171,169,167,109, .5, 126.9, 126.8, 123.9, 118.8, 115.5 2, 152.1, 140.6, 132.9, 126.3, 124.9, 122.8, 116.5, 115.2, 56.4, 23.4 2, 151.1, 143.4, 131.8, 128.4, 125.9, 123.2, 121.9, 112.9, 25.0 149.1, 134.4, 132.1, 126.6, 124.7, 123.3, 54.1, 35.9 145.5, 135.4, 128.6, 127.4, 124.9, 124.5, 79.9, 48.5 8,146.8,133.7,128.6,126.5,21.7,43.9;MS (CI) 5, 146.7, 133.6, 130.8, 128.6, 126.9, 123.0, 66 …”
Section: -Chloroacetanilidementioning
confidence: 99%
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“…7, 149.9, 133.3, 128.8, 127.2, 124.7, 124.5, 61.0, 24 = 7.8,1.5 Hz,1H),1H),2H),3.90 (s,3H);13 C NMR (75 MHz,CDCl3) δ 155.0,130.3,127.8,122.4,121.3,112.1, 4-Chloroanisole (10c): 7.19 (dd,J = 8.8,2.4 Hz,1H),6.85 (d,J = 8.8 Hz,1H),3.89 (s,3H); 13 C NMR (50 MHz, CDCl 3 ) δ 152. 2,128.3,125.9,123.9,121.6,111.1,54.7;MS (EI) ), 201,199,197 (100),195,171,169,167,109, .5, 126.9, 126.8, 123.9, 118.8, 115.5 2, 152.1, 140.6, 132.9, 126.3, 124.9, 122.8, 116.5, 115.2, 56.4, 23.4 2, 151.1, 143.4, 131.8, 128.4, 125.9, 123.2, 121.9, 112.9, 25.0 149.1, 134.4, 132.1, 126.6, 124.7, 123.3, 54.1, 35.9 145.5, 135.4, 128.6, 127.4, 124.9, 124.5, 79.9, 48.5 8,146.8,133.7,128.6,126.5,21.7,43.9;MS (CI) 5, 146.7, 133.6, 130.8, 128.6, 126.9, 123.0, 66 …”
Section: -Chloroacetanilidementioning
confidence: 99%
“…Various oxidative chlorination agents such as sulfuryl chloride, 3 N-chlorosuccinimide, 4 copper(II) chloride, 5 titanium tetrachloride, 6 trifluoromethanesulfonyl chloride, 7 para-toluenesulfonyl chloride 8 and acetyl chloride, 9 have been reported in this context. In addition, combination systems based on mixtures of diverse oxidants, i.e., perchloric acid, manganese(III) acetate, hydrogen peroxide, LDA, sulfuric acid, oxone ® and dimethylsulfoxide with chlorine sources have been developed to generate chlorine.…”
Section: Introductionmentioning
confidence: 99%
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“…34 To a stirred solution of THF (100 mL) and 2.0 M solution of lithium diisopropyl amide in heptane/THF/ethylbenzene (12.0 mL, 24.0 mmol), a solution of 1,4-dipropionylbenzene (3) (2.05 g, 10.8 mmol) in THF (50 mL) was added dropwise at À78 C and the reaction mixture was stirred for 1 h. Then the temperature of the mixture was allowed to rise at room temperature. A solution of p-toluenesulfonyl chloride (4.51 g, 23.7 mmol) in THF (50 mL) was added slowly to the reaction mixture at room temperature and the reaction mixture was stirred for 18 h. 6.…”
Section: Synthesismentioning
confidence: 99%
“…Electrophilic halogenating agents are useful for halogenating these carbonyl compounds and nitrogen heterocycles. In general, direct conversion of carbonyl compounds such as ketones to a-halocarbonyl compounds can be achieved by using halogenating agents such as copper(II) halides, 6 sulfuryl chloride, 7 p-toluenesulfonyl chloride, 8 N-halosuccinimide/p-toluenesulfonic acid, 9 Koser's reagent/ magnesium halides, 10 tetraalkylammonium trihalides 11 and bromine. 12 Recently, much effort has been made to develop new efficient methods for a-halogenation of 1,3-dicarbonyl compounds.…”
mentioning
confidence: 99%