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By Alfredo Ricci
The following, essentially the most very important useful crew in natural chemistry is mentioned in a single convenient quantity. The monograph covers its software -- from normal items to man made prescribed drugs -- detailing complicated syntheses utilizing the amino staff as templates and sleek recommendations focussing at the creation of the amino workforce. A definitive must-have for each chemist.
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Extra resources for Amino Group Chemistry: From Synthesis to the Life Sciences
Example text
65). 65 in MeOH (400 mL) and the mixture was heated at 50–60 °C. 4 mmol) was added portionwise to the yellow solution. 5 h. Conc. 7 M, 280 mL, 196 mmol) was added to the vigorously stirred mixture over 40 min. When the addition was complete, the mixture was cooled to 0 °C and diluted with CH2Cl2 (400 mL), and the resulting biphasic mixture was warmed to 23 °C and stirred for 15 min. The contents were transferred to a separating funnel with H2O (200 mL), the organic phase was isolated, and the aqueous layer was extracted with CH2Cl2 (200 mL).
50, with cis-β-methylstyrene I as a specific alkene. Initially the styrene reacts with a Br+ source to give the bromonium cation II, and nucleophilic attack by TsN−Cl then affords a bromoaminated intermediate III. Attack either of Br− or of TsN−Cl on the N–Cl group in III gives sulfonamide anion IV, which cyclizes intramolecularly to afford aziridine V. The regenerated Br–X initiates another catalytic cycle. 50 Catalytic cycle of bromine-catalyzed aziridination. 51) [60]. When 2 molar amounts of styrene are added to chloramine-T (29) in the presence of a catalytic amount of iodine in a 1 : 1 mixture of CH3CN and a neutral buffer, for example, the corresponding aziridine is obtained in 91% yield.
41 Aminochalcogenation of alkenes by chloramine-T (29). 42 OsO4-catalyzed aminohydroxylation of alkenes by chloramine-T (29). 43 over the stoichiometric oxyamination reactions [50]. This reaction is an aza analogue of the catalytic dihydroxylation of alkenes. The sulfonylimido osmium 31 is proposed as the key species. 43) [51]. 44). The N-chloro benzyloxycarbamate salt 32 is prepared in situ from benzylcarbamate, NaOH, and tert-butyl hypochlorite [52]. 45) [53a]. 3 Aziridination of Alkenes Aziridines can be used as synthetic intermediates in the preparation of nitrogencontaining compounds through ring-opening and ring-expansion reactions.