Preparation Oxaziridines from Olefins

Advances in the Chemistry of Oxaziridines

“… 28 In addition, N -H oxaziridines have also been obtained via photolysis of hydroxylamines, 29 oxidation of ketimines by peracid, 30 and ozonolysis in the presence of ammonia. 31 …”

Peracid oxidation of imino ethers

“…Following the reaction by low-temperature nmr showed the buildup of 19a at the expense of azetine 18a, with no detectable intermediate. Oxidation methylazetine (22) with an excess of MCPBA results in a mixture of 2-methoxy-4,4,5-trimethyloxazoline (23) and methyl 2,3-dimethyl-3-nitrosobutanoate (24). A 53% yield of products containing 73% of 23 and 27% of 24 is obtained.…”

“…The data for the aldehyde are bp 60°(1-2 mm) [lit. bp 84-85°(12 mm)66]; ir (CH2C12) 2940, 2900, 2830, 2730, 1730 cm"1; nmr (CH2C12) 1.16 (t, J = 7.3 Hz, 3 H), 2.64 (four-peak m, 4 H), 4.12 (q, J = 7.3 Hz, 2 ), 9.70 (t, J < 1 Hz, 1 H); mass spectrum (70 eV) m/e (rel intensity) 115 (M+, 1.2), 114 (2), 101 (10), 73 (3), 59 (3), 57 (2), 56 (2.5), 55 (6), 45 (4), 44 (2.5), 43 (2.5), 29 (7), 28 (18), 27 (4), 18 (100), 17 (24).…”

“…1.50-2.00 (m, 4 H), 2.00-2.50 (m, 4 H), 3.68 intensity) 141 (M+, 0.4), 139 (1), 110 (24), 83 (5), 82 (60), 81 (8), 74…”

“…(90), 69 (8), 68 (24), 59 (87), 55 (100), 54 (33), 53 (12), 43 (40), 42 (29), 41 (78), 39 (33). The data for 36 are bp 120°(0.1 mm); ir (CCI4) 3580, 3250, 2930, 2850, 1745 cm-1; nmr (CC14) 1.40-2.00 (m, 4 ), 2.00-2.50 (m, 4 H), 3.65 (s, 3 H), 6.67 (t, J = 5.5 Hz, 0.42 H, anti), 7.36 (t, J = 6.0 Hz, 0.57 H, syn), 8.70 (br s, 1 H); mass spectrum (70 eV) m/e (rel intensity) 143 (M+ -16,0.2), 110 (22), 82 (25), 74 (41), 68 (9), 59 (28), 55 (31), 54 (9), 43 (38), 42 (22), 41 (25), 39 (13), 29 (16), 28 (22), 27 (16), 18 (100), 17 (22), 15 (19).…”