Oxaziridine, 2-/-butyl-3-phenyl

Oxaziridine, 2-/-butyl-3-(4-nitrophenyl)-hydrolysis rate constant, 7, 207 (71JCS(B)778) Oxaziridine, 2-/-butyl-3-phenyl- 7, 205 (57JOC1263) hydrolysis rate constant, 7, 207 (71JCS(B)778) Oxaziridine, 2-ethyl-3-(4-methoxyphenyl)-UV, 7, 201 (B-67MI50800)... 

In some cases acid amide formation was observed on attempted deprotonation at oxaziridine ring carbon. 2-r-Butyl-3-(4 -nitrophenyl)oxaziridine (67) was converted to the anion of acid amide (68) by sodium amide (69TL3887), while 2-(4 -nitrobenzoyl)-3-phenyl-oxaziridine (69) afforded the diacylimide (70) by addition of cyclohexylamine to its benzene solution at room temperature (67CB2593). 

Methyl-4-phenyl- El6a, 317 (red. Oxim —N-Methyl.) Oxaziridin 2-tert.-Butyl-3-(2-phenyl-ethenyl)- E14a/2, 529 (Imin + Persiiure)... 

Earlier 3-phenyl-2- /t-butyloxaziridine 129 was reported not to be able to oxidize sulfides to sulfoxides even on heating and to undergo thermal rearrangement to A -/r /z-butyl-a-phenylnitrone. However, Shimizu et al. demonstrated that under 800 MPa at 100 °C, this oxaziridine behaves as an oxidant and was able to oxidize thioanisole to the sulfoxide <1997J(P1)3491>. 

Acid hydrolysis of oxaziridines was investigated kinetically and found to be of first order and Ho-dependent. 2-t-Butyl oxaziridines with an alkyl or aryl group in position 3 (16) were studied. The acidity-rate-profile approximated a constant rate given by complete protonation of 16. pK values are between -1-0.13 and —1.81, rate constants of hydrolysis in dilute perchloric acid at 25°C are 43.4 x 10 min (R = p-nitrophenyl) and 1.49 x 10 min (R = phenyl). O-Protonation is assumed to be followed by C—O bond cleavage (16a). In the case of 3-alkyloxaziridines there is considerable competition from O—N bond cleavage. 

The Movassaghi group has investigated the stereoselective C2 to C3 migration of a 2-phenyl substituent on diastereomerically pure hydroxyindolenines 13 [18]. The requisite hydroxyindolenines were prepared via oxidation of 2-phenyl L-tryptophan with Davis oxaziridine (3-n-butyl-l,2-benzisothiazole-l,1-dioxide oxide). The oxidation step proceeded with modest diastereoselectivity, providing a 2 1 mixture of the (3R) and (35)-hydroxyindolenines 13 that were separated. As illustrated for... 

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