Molecular Rearrangement of Sulfanilides. I

Moore, Maurice L.; Johnson, Treat B.

doi:10.1021/ja01312a002

Cited by 18 publications

(7 citation statements)

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“…By following a reported procedure, 25 in a round-bottom flask, 2-nitrophenylsulfenylchloride (190 mg, 1.0 mmol) was dissolved in anhydrous CH 2 Cl 2 (2.5 mL) and a solution of the corresponding aniline derivative (3.0 mmol) in anhydrous CH 2 Cl 2 (3.8 mL) was added under argon. After 2 h stirring at r.t., the precipitated hydrochloride was filtered over a plug of alumina, washed with CH 2 Cl 2 (20 mL) and the solvent was evaporated under vacuum.…”

Section: Preparation Of Protected Anilines 5; General Procedures Gp1mentioning

confidence: 99%

Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbonates

et al. 2018

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An organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates with aromatic amines in the presence of β-isocupreidine is described. Chiral allylic amines were obtained in almost quantitative yields (90–96%) with moderate enantioselectivity. Recrystallization afforded products in good yields (45–73%) and high optical purity (82–99% ee). This method provides a facile and efficient route to obtain optically active β-lactams, including the building block of the cholesterol-lowering drug Ezetimibe.

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Section: Preparation Of Protected Anilines 5; General Procedures Gp1mentioning

confidence: 99%

Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbonates

et al. 2018

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“…In the case of dibenzyl disulfide (10a) this reaction resulted in the formation of benzyl chloride (Ila). The reaction was assumed to proceed oia the formation of 9a as the intermediate in the decomposition of benzylsulfur trichloride (12).…”

Section: R-mentioning

confidence: 99%

In Search of New Sulfur Transfer Agents

Sosnovsky

Krogh

1982

Liebigs Ann. Chem.

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Dedicated to Professor Dr. L. Horner on the occasion of his 70th birthday.The chemistry of various sulfur-transfer agents is studied. The reaction of aromatic sulfenyl chloride 5 in the presence of imidazole and/or triethylamine gives the aryl disulfides 7 in 14 -85 percent yield, whereas in the case of the corresponding benzylsulfenyl chlorides 9 in the presence of triethylamine and/or caprolactam, both disulfide 10 and benzyl chlorides 11 are formed in 0 -81 percent and 10 -72 percent yield, respectively. Untersuchungen iiber neue Schwefelubertragungs-ReagenzienDie Reaktionen verschiedener Schwefelubertragungs-Reagenzien werden untersucht. Die Reaktionen von aromatischen Sulfenylchloriden 5 ergeben in Gegenwart von Imidazol und/oder Triethylamin die Aryldisulfide 7 mit 14-85% Ausbeute, wahrend bei den entsprechenden Benzylsulfenylchloriden 9 in Gegenwart von Triethylamin und/oder Caprolactam sowohl die Disulfide 10 als auch die Benzylchloride 11 mit 0-81 % bzw. 10-72% Ausbeute entstehen. -iibertragungsreaktionen zwischen 3-Sulfenohydantoinen 18 und Aminen sind fur die Darstellung von unsymmetrischen Sulfenamiden 20 brauchbar (31 -61 Vo Ausbeute). Entsprechende Reaktionen von 23 und 24 mit Piperidin liefern N,N'-Thiodipiperidin (3, X = CH,) mit 71 -80% Ausbeute.

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“…Heating of sulfenyl halides generally leads to disulfides; the process seems to be facilitated in the presence of a tertiary amine. Thus, 4-acetamino-lnaphthalenesulfenyl bromide hydrobromide decomposed to the disulfide when heated (116), and 2-nitrobenzenesulfenyl bromide when heated with pyridine likewise gave 2-nitrophenyl disulfide (74). Sulfenyl halides also react with hydrogen sulfide to form trisulfides.…”

Section: Formation Of Disulfidesmentioning

confidence: 99%

“…M.p. 74.5-76°C. From 2, 4-dinitrobenzenesulfenyl chloride and potassium thiocyanate, by shaking for 20 hr.…”

Section: B Tabulation Of Sulfenyl Thiocyanatesmentioning

confidence: 99%