1983
DOI: 10.1021/jo00168a040
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Bis(methoxycarbonyl)sulfur diimide, a convenient reagent for the allylic amination of alkenes

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Cited by 52 publications
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“…[36] Indeed, heating 52 overnight at 60°C under the reaction conditions resulted in full conversion of initially formed 54 to the more stable Zaitzev isomer 53 E+Z in high yield. The reactions at room temperature were not regioselective.…”
Section: Introductionmentioning
confidence: 96%
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“…[36] Indeed, heating 52 overnight at 60°C under the reaction conditions resulted in full conversion of initially formed 54 to the more stable Zaitzev isomer 53 E+Z in high yield. The reactions at room temperature were not regioselective.…”
Section: Introductionmentioning
confidence: 96%
“…It was considered possible that the initially formed Hofmann elimination product (54 and 57) isomerized partly to more stable isomers (53 E+Z and 54 E+Z). [36] Indeed, heating 52 overnight at 60°C under the reaction conditions resulted in full conversion of initially formed 54 to the more stable Zaitzev isomer 53 E+Z in high yield. These isomers (53E and 53Z) were separately con- firmed to be stable on heating under the reaction conditions.…”
Section: Introductionmentioning
confidence: 96%
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“…Following General procedure 4, 46 (980 mg, 10.0 mmol), Bi (OTf) 3 (328 mg, 0.50 mmol), KPF 6 (92 mg, 0.50 mmol), methyl carbamate (1.13 g, 15.0 mmol) and MgSO 4 (w1.5 g) in THF (50 mL) were reacted for 16 h to give, after purification by flash column chromatography (eluent 30e40 C petrol/EtOAc, 1:0 to 9:1 gradient elution), 59 as a white solid (1.21 g, 78%);72 mp 25e26 C; d H (400 MHz, CDCl 3 ) 1.47e1.55 (1H, m, CH 2 ), 1.56e1.66 (2H, m, CH 2 ), 1.84e1.92 (1H, m, CH 2 ), 1.94e2.00 (2H, m, CH 2 ), 3.64 (3H, s, OMe)…”
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confidence: 99%
“…Extensive work has been done in the area of allylic halogenation and oxidation of fats and oils (1)(2)(3), but formation of allylic amines has received limited attention. It was reported that bis(N-p-toluenesulfonyl) sulfodiimide (1) may react with alkenes to form N-(allylic alkenyl) sulfinamidines (4,5). Allylic amination has been investigated (6-10), but these reactions have not been applied to fats and oils.…”
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confidence: 99%