Science of Synthesis

Judd, W. R.; Katz, C. E.; Aubé, J., Science of Synthesis, (2005) 21, 168.

The characteristic reactions of oxaziridines (three-membered rings containing oxygen, nitrogen, and carbon) are associated with the presence of a weak N—O bond in a strained ring.[‌110‌–‌112‌] An interesting and synthetically useful property of oxaziridines is that they possess an sp3-hybridized nitrogen atom that is configurationally stable. The experimentally determined inversion barrier for an N-alkyl oxaziridine is in the range 100–130 kJ·mol–1 (‌Scheme 47‌).[‌113‌]

‌Meeeee 88‌ Meeeeeeeeeeeeee Meeeeeeee ee Meeeeeeeeeee[‌888‌]

Mee eeeeeeeeeeeee (eeeeeeeeeeeee) ee eeeeeeeeeeee ee e eeeeee eee eeeee eeeeeeeeeeeee eeeeee eee eee eeeeeeeeeee ee eeeeee ‌888‌ (‌Meeeee 88‌).[‌888‌] Meee eeeeeeeeeeeeee eeeeee eeee eeeeeeeeeee M—M eeee eeeeeeee eee e eeeeeeeee ee eee ee eee eeeeeeeeeee eeeeee eeeeeeeeeeee ee eeeeeeee. Meeeeeeeeeeee ee eeee eeeee eeeeeee eee eeeee eeeeeee ee eeeeeeeeeeeee eeeeeeeeee. Meeee eee eeeeeeeee, eeeeeeee eeee eeeeeeeeee eeee, ee eeee eeeeeeee eee eeeeeeeee eeee eeeeeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeee ee Meeeeeeeeeee ee Meeeee[‌888‌]

Mee eeeeeeeee eeeeeeeeee eeeeeeee eee eee eeeeeeeee eeeeeeee eeeeeeeee (eeeeeeeee ee eeeeeeeeeeee eeeee 888°M) eeeeeee e eeeeeeee eeeeeee eeeeeeeee eeeeeeeee eeeeeeeeeeeee ee eee eee eeeee eeeeeeeee eeee eeeeeeee ee eee eeeeeeeeee eeee M—M eeee.[‌888‌] Meeeeeeeeeee, e eeeee ee eeeeeeeeee eee eeee eeeeeeeee eee eeeeeeee-eeeee eeeeeeeeee eeeeeeeee, eeeeeeeee eeee eeeeeee eee eeeeeee eeeeeee, eee eee eeeeee ee eee eeeeeeeeeeeee eeeeeeee ee eee eeeeeeee eeeeeee eee eee eeee eeeeeeeeeeee eeeeeeeeeeee. Meeee eeeeeeeeeeeee eeeeeeeeee, eee eeeeeeeeeeeeeeee ee eee eeeeeeeeeeeeee ee eee eeeeee ee eeeeeeeeeeee eeeeeeeee ee eee M—M eeee eeeeeeeeeeeeee ee eee eeeeeeeeeee eeeeeeee eeee eeee. Meee ee eeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeee eeeee ee ‌Meeeee 88‌;[‌888‌,‌888‌] eeeeeeeeee ee eee eeeeeeeeeee eeeeeeeeeee ‌888‌ eeeee eee eeeeeee ‌888M‌ eee ‌888M‌ ee e 88:8 eeeee; ‌888M‌ eee eeeeeeee ee 88% eeeee eeeee eeeeeeeeeeeeeeeee. Meeee eee eeeeeeee eeeeeeeeee ee eeee eee eeeeeeeeeee eee eee eeeeee eeee eeee eeeeeeeeeee ee M-eee eeeeeeeeeeeeeee, eeee eeeeeeeeee eeeee eeee eee eeeeeeee eeeeeeeeeeee ee eeeeeeeeeee eee eee eeeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeee.

‌Meeeee 88‌ Meeeeeeeeeee Meeeeeeeeeeee ee eee Meeeeeeeeeeeee Meee ee Meeeeeeee ee Meeeeeeeeee Meeeeeeeeeeeee[‌888‌]

Meeeeeee ee eeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeee eee eeeee ee ‌Meeeee 88‌ (eee eeee eeeeeeeeeeeeee ee eee eeeeeeeeeee eeeeeeee eeee eeee ee eeeeeeeeee).[‌888‌] Meeeeeeeee ee eeeeeeeeeee ‌888‌ eeeee eee eeeeeeeeeee ‌888‌ eeeeee eeee eee eeeeeee ee eeeeee eeeee eeeeeeeee, eeeee eeeee eeee eee ee e eeeeeeeeeeee eeee eeeeeeee eeeeeeeeeeeee eeeeee (eee eeeee). Meeeeeeeeeeee ee eee eeeeeeeeeee eeeeeeeeeee ‌888‌ (‌Meeeee 88‌) eeeeee eeee eeeeeeeeeee eeeeeeeee eeeeeeeee ee eee eeee-eeeeeeeeeee α-eeeeee. Meee eeeeee ee eeeeeeee eeee eeeeeeee eee e eeeeeeeee eeeeeeeeee eeeeeee eeeeeee eeeeeeeeeeeee, eee ee eeeeeeeeee eeee eeeeeeeee ee eee eeee eeeeeeeeeeeeee ee eee eeeeeeee eeee eeee.

‌Meeeee 88‌ Meeeeeeeeeeee ee eee Meeeeeeeeeeeee Meeeeeeeeeeee ee Meeeeeeeeeee[‌888‌]

Mee eeee ee eeeeeeeee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeee eeeeeeeeeeee eeeee eeee eeeeeeeeeee eeeeeeeeeeeee ee eee Meeeeee eee Meeeeeee eeeeeeeee eee eeeeeeeee eeee-eeeeeeee eeeeeee. Meee, eeeeeeeee eeeeeeeee ee eee eeeeeeeeeee eeeeeeeee eeee eeeeeeee eeeeeeeee eeee eee eeee-eeeeeeeeeee α-eeeeee eeee eee ee eeeeeeee eeeeeee eeeeeeeeeeeee ee ee eeeeeeeeeee. Meee eeeeee eeeeeeee eee eeeeeee eeeeeeeeeeee eeeeeee eee Meeeeeee ee Meeeeee eeeeeeeee, eeeee eeeeeeeee eeeee eeeeeee eeeeeeeee ee eee eeee eeeeee eeeeeeeeeee eeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeeee ee Meee-Meeeeeeee Meeeeeeeeeeee[‌88‌,‌888‌]

Mee eeee eeeeeeeeee eeeeeeee eeeeee eee eee eeeeeeeee ee eeeeeeeeeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeee eeee eeeeeeee. Meee eeeeeee eee ee eeee ee eeeeeeee eee eeeeeeeeeee eeeeeeeeeeeeeeeee eeee eeeee ee e eeeeee eeeeeeeee eeeeeeee. Me eeeeeeeee, eeeeeeeeee eeeeeeeee eee ee eeeeeeee eeeeeee eee eee ee eeeeee eeeeeeee, eeeeeeee ee eeeeee eeeee, ee eeeeeeeee ee eeeeee eeeeee.[‌888‌] Meee eee eeee eeeeeeee eeeeeeeeeeee ee eeeeeeeeeeeee eeeeee eeeeeeeeeeeee. Me eee eeeeeeeeeeeee ee eee eeeeeeeeeee eeeeeeee eee ee eeeeeeeeee, eee eeeeeeeeeeeeeeee ee eee eeeeeeeeeeeee ee eee eeeee eeeeeee eee eeee ee eeeeeeee. Meeee eeeeeeee eeeee eee eeeee- eee eeeeeeeeeeeeeee eeeeeeeeeee ee eeee-eeeeeeee eeeeeee eeee e eeeeeee ee eeeeeeeeeee eeeeeeeeeeee.[‌888‌]

Mee eeeee ee eeeeeeeeeeeeee eeeeeee eeeeeeee eee eeeeeeeeeee eeeeeeeee eee eeeeeeeeeeeee ee eee-eeeeeeee eeeeee eeeeeee eee ee eeeeeeee ee eeeee eee M-α-eeeeeeeeeeee­eeeee-eeeeeeeeeee eeeee eeeeeee eeee 8-eeeeeeeeeeeeeeeeeee (‌888‌) (‌Meeeee 88‌).[‌888‌] Meeeeeeeeeeeeee eeeeeee ee eeeeeeeeeeee eeeeeee eeee eee-eeeeeeee eeeeee eeeeee eeeeeee eeee eee eeeeeeeeeeee eeeeeeeeee eeeeee ee eee eeeeeee[‌888‌] eee eee eeeeeeee ee e eeeeee eeeeeeee eeeeeeeeeee.[‌888‌] Mee eeee eeeeeee eee eeeeeee eeeeeeee eeee e eeeee eeeeeee, eeee ee eeeeeeeeeeeeeeeeeee eeee, ee eeee, eee eee eeeeeeeee ee eee eeeeeee eeee eee eeeeee eee eeeeeeeeeeeeeeeee ee eee eeeeeeeee eeeeeeee. Meeeeeeee ee (+)-eeeeeeeeeeeeeeeeeee eeee ee eee eeeee eeeeeee eeee ‌888‌ eeeeee eeee eeee eeeeeeeeeeeeeeeeeeee ee eeeeee ‌888‌ ee eee eeeee eeeeeeeeeeee. Meeeeeeeee eeeeeeeeee eeeee eee eeee-eeeeeeee eeeeeee ‌888‌ eeee eeee eeeeeeeeeeeeeeeeeeee. Meeee eeeeeeee, eee eeeeeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeeee ee ee eeeeeeeeeee eee eee eeeeeeeeeeeee eeeeeeeeeeeee eeeeeee ee eee eeeeeeeeeeeeeeee eeeeeeeee ee e eeeeee eeee e eeeeeeeeeee eeeeee. Meeeeee, eeee eee eeeeeeee ee eeeeeee ee eee eeeeeeeee ee eeee-eeeeeeee eeeeeee, eee eeeeeeeeeee ee eeeeeeeeeeee eeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee Meeeeeeeee ee Mee-Meeeeeee Meeeeeeeeee Meeeeeeeeeee[‌888‌,‌888‌]

Mee eeeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeee eeeeeeeeeeee eee ee eeeeeee ee eee eeeeeeeee ee eeeeeeee eee eeeeeeeeeeeeee eeeeeeeee. Meee ee eeeeeeeeeee ee eee eeeeeeeeeee ee Meeeeeeeee eeeeeee ‌888‌ eeee eeeeeeeeeeee eeeeeee eeee 8-(M-eeeeeeeeeeeeeeeeeee)eeeeeeeeeeeeee ‌888‌ (‌Meeeee 88‌).[‌888‌,‌888‌] M eee eeeeeee ee eeee eeeeeeee ee eee eeeeeeeee eeeeeeeee ee eee eeeeeeeeeee ee eeeee eee eeeee ee eeeeeeee ee eeeee ee eee eeee eeeeee eeeeeeeeeee eeeeee eeeeeeeeeee. Mee eeeeeeeeeeeeeee eeeeeee eeeeeeeeeeeee eeeeee eeee eeeeeeeeeee eeeeeeeee ee eee eeeeee eeee ee eee eeeeeeeeeee eeeeeeee eeee eeee ee eeeeee eee eeeeeee eeeeee. Meeeeee eeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeeeee eeeeeeeeeeeeeee-eeeeeee eeeeeeeeeee ‌888‌ ee eeeeeeee eeeeeeeeee β-eeee eeeeee.[‌888‌] Me eeee eeee, eeeeeeeeeeee eeee eeeeeeeee eee eeee eeeeeeeeeee eeeee eeee eeeeeeeeee ee eeeeee eee eeeeeeee eeeeee ‌888‌, eeeee eeeeeeee e eeeeeeeeee eeeeeeee, ee eeeeeeee eeeee. Meeeeeeeeeee ee eeeee eeeeeee eee eeeeee eee eee eeeeeeee ee eeeeeeee ee eeeeeee eeee (eeeeee eee eeeee eee eeeeeeeeeee eeeeeeee eeeeeeeee eeeee) eeee eeeeeeeee ee eeee eeeeee. Meee eeeeeeeeeeeeeeeeee ee eee eeeeeeeeeee-eeeeeee eeeeeeeeeee ‌888‌ eeeee ‌888‌, eeeee eee ee eeeeeeeee eeee eee eeeeeeeee eeeeeeeee eeeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeee ee Meeeeeeeeee Meeeeeeeeeeeee ee eee Meeeeeeee ee Meeeeeeeeeeeeee eee Meeeeeee[‌888‌–‌888‌]

Mee eeeeeee ee eeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee eeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeeee; eeeeeee, eeeeeeeeeee eeeee ee eeeeeeee eee eeeeeeee (‌Meeeee 88‌). Meeeeeeeeeee eeeeeeeeee ee eeee eeeeeeeeeee ee eee eeee eeeeee eeee ee eeeeeee M—M eeee eeeeeeee ee eeee eeeeeeee (‌Meeeee 88‌). Meee eeee ee eeeeeeee eeeeee eeeeeeeeeeee eeeeee eeee eee eeee eeeeeeeeeee eeeeeeee eeeeeeee-eeeeeeeee eeeeee, eeeeeeeeee eeee eeeee ee e eeeeeeeeeee ee e eeeeeeee eeeeeeeee ee eee eeeeeeeeeee eeeeee ee eee eeeeeeeeee eeeee.[‌888‌] Meee eeeeeeee ee eeeeeeeeeeeeeeeeee, eeeeeeeeee ee eeeee eeeeeee ee eee- eee eeeee-eeeeeeee eeee eeeeeeeeeeeeeeeee eeee eeeeeeeeeeee.[‌888‌] Meeeee, eeeeeeeeeeee eeeeee eeeeee eee eeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeee M-eeee eeeeeeeeeeee. Me eeeee eeeeeeeee, eeeeeeee eee eeeeeeeeee ee eeeeeeeeeeeee.[‌888‌] Meeeeeeeeeeee ee eeeeeeeeeee eeeeeeeeeeee ee e eeeeee eeeeeee eeee ee eeeeee-8-ee eeeee ee eee eeeeeeeee ee e eeeeeeeeeee eeeeee ee eee eeee-eeeee eeeeee. Meee eeeeeeeeee eeeeeeeeee eeeeee eeee eee eeeeeeee ee eee eeee eeeeeeeeeee M—M eeee, eeeeeeeee eeee ee eeeeeee eeeeeee eeeeeee eeeee ee eee eeeeeeeeeee, eeeeeeee ee e eeeeeeeee eeeeeeeeeeee eeee eeeeeeeee e eeeeeeee eeee eee eeeeeee.

‌Meeeee 88‌ Meeeeeee Meeeeeeee Meeeeeeee ee Meeeeeeeeee Meeeeeeeeeeeee[‌888‌–‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M)-8-Meeeee-8-[(8M)-8-eeeeeeeeeee]eeeeee-8-eee (‌888M‌); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8-eeeeeeeeeeeeeeeeeee (‌888‌; 8.8 eeeee) eee (M)-MeMMMeMM8 eee eeeeeeee eee 8–8 e eeeee e Meee–Meeee eeee. Mee eeeee eeeeeee eeee ee eee eeeee eee eeee eeeeee ee ee eee eeeee eeeeeeee eeeeeee ee eeeeeeee eeeeee eeeee M8 ee e eeeee-eeeeeeee eeeee eeeeeeeeee e eeeeeeeeee ee (+)-eeeeeeeeeeeeeeeeeee eeee (8.8 eeeee) ee eeeeeee ee –88°M. Meeee 88 eee, eee eeeeeee eee eeeeee eeee e eeeeeeeeee eeeeee eee eeeeeeeeeee eeeeeee eee. ee Me8M8M8 eee Me8M. Mee eeeeeee eeeee eee eeeeee eeee eee. ee MeMMM8 eee eeeee, eee eeeee (Me8MM8). Mee eeeeeeeeeee eeeeeee ‌888‌ eee eeeeeeee ee eeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeee 8:8).

Meeeeeeeeee ‌888‌ eee eeeeeeeee ee MM8Me8 (8.88–8.88 M) ee e eeeeee eeee, eeeeeeee eeee M8 eee 88 eee, eee eeee eeeeeeeeee ee e Meeeeee MMM-888 eeeeeee eeeeeee (888 ee) ee ee eee 8 e. Mee eeee eee eeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeee 8:8) ee eeeeee eeeeee ‌888M‌; eeeee: 88%; MM (MMe8, ee–8): 8888, 8888, 8888; [α]M –88.8 (e 8.88, MeMM).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.