Tosylchloramide → trans-2,3-Diethyl-1-[(4-methylphenyl)sulfonyl]aziridine

Participants

Reaction Steps

General procedure (described for trans-3-hexene) as illustrated in FIG. 2, entry 1: To a mixture of trans-3-hexene (252 mg, 3 mmol; see above discussion for employable olefins (FIG. 1); 1.0 equivalents used) and anhydrous N-sodio-N-chloro sulfonamide (chloramine T/751 mg, 3.3 mmol; see above discussion for employable salts or chloramine trihydrates (chloramine T trihydrate can be effectively used in the same concentration); effective range: 1.0-2.0 equivalents; optimal concentration 1.1 equivalents) in CH3CN (15 ml, 0.2 Molar; see above discussion for employable solvents; effective range: 0.01 Molar to 1.0 Molar) was added PTAB (113 mg, 0.3 mmol; effective range: 0.05 to 0.50 equivalents; optimal concentration: 0.10 equivalents) at 25° C. (effective range 25° C. to 60° C.). After vigorous stirring for 12 h (time can vary from 1 h- to 24 h depending on scale and substrate). The reaction mixture was worked up using standard workup conditions. A typical procedure may be carried out as follows: The reaction mixture was concentrated (about up to 1/10 volume) and filtered through a short column of silica gel (4×4 cm, 10% EtOAc in hexane). After evaporation of the solvent, the resultant solid was purified by recrystallization in hexane to give 710 mg (93%) of trans-2,3-diethyl-1-[(4-methylphenyl)sulfonyl]aziridine as colorless crystals; 1H NMR (CDCl3400 MHz)δ7.81 (d, J=8.2 Hz, 2H), 7.28 (d, J=8.2 Hz, 2H), 2.56-2.61 (m, 2H), 2.40 (s, 3H), 1.63-1.79 (m, 4H), 0.90 (t, J=7.5 Hz, 6H); 13C NMR (CDCl3, 100 MHz) d 143.7, 137.9, 129.4, 127.4, 50.9, 23.2, 21.5, 11.7; MS (FAB, NBA/NaI): 254 (M+H)+; HRMS (FAB, NBA/NaI): calculated for C13H19NO2S (MNa)+276.1034, found 276.1029; m.p. 69-70° C. (hexane).

Provenance & Evidence