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18.6.3.1.3.1 Method 1: Reaction with Isocyanates

DOI: 10.1055/sos-SD-018-00578

Rossi, L., Science of Synthesis, (2005) 18, 571.

The reaction of oxiranes with organic isocyanates to yield oxazolidin-2-ones is a very famous and exploited reaction. The synthesis usually takes place at elevated temperatures in organic solvents (acetonitrile, dioxane, benzene) or in the absence of solvents (‌Scheme 156‌). Catalysts may be used if necessary; usually they are secondary or tertiary amines, quaternary ammonium halides, carboxylate anions, zinc, iron, or lithium chlorides, complexes of aluminum, zinc, or iron halides with ethers, amines, amides, sulfoxides, or phosphines. When the starting oxirane is asymmetric, a possible mixture of regioisomers (‌220‌, ‌221‌) might be obtained. The regioisomer ratio usually depends on the reaction conditions adopted.

‌Meeeee 888‌ Meeeeeee ee Meeeeeee eeee Meeeeeeeeee[‌888‌,‌888‌–‌888‌]

Mee eeeeeeeee ee eee eeeeeee eee ee eeeeeeeee ee eeeeeeee eee eeeeeeeee eeee ee eeeeeee eee eeeeeee eeee. Me e eeeeeee eeee, eee eeeeeee ee eee eeeeeee eeee, eee eeeee eee eeeeeeeee ee e eeeeeeeeee eeeeeeee eeeeeeeeee-8-eee ‌888‌, eeeeeee ee eee eeeeeeee eeeeeeee eee ee eee eeeeee ee eee eeeeeeeeeee ee eee eeeeeee. Mee eeeeeee, ee eee eeeeeeee ee eeeeeee, eee eeeeeee eeee eeeeeeee ee eee eeeeeeeeee eeee eeeeeeeee ee ee eeeeeeeee eeeeeee ‌888‌ (‌Meeeee 888‌). Me eee eeeeeeee ee eeeeeeeeee eeeeeeee eeeee, eeeeeeeeee-8-eeee eee eeeeee eee eee eeeeeeeeeeee ee eee eeeeeee eeee eee eeeeeeeee eeeeeeee ee eeeeeeee ee eee eeeeeeeeee eeee eeeeeeee eeeeeeee eeeee ee eeeee eeeeeee ee eee eeeeeee eeeeeeee. Mee eeee ee eee eeeeeeeeee eeeeeeee eeeee ee ee eeeeeee eee eeeeeeeeeeee eeeeeeeeee ee eee eeeeeeeee eeeeeeee. Meee eeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeee eeee eeeeeeee eee eeeee ee ‌Meeeee 888‌.

‌Meeeee 888‌ Meeeeeeee Meeeeeee ee Meeeeeee eeee Meeeeeeeeee[‌888‌,‌888‌–‌888‌]

‌Meeeeeeeeee 888‌

M8 M8 M8 M8 Meeeeeee Meeeeeeeee Meeee (%) ee ‌888‌ Mee
e-Me MM8Me M M MeMe, eeeeeee, M8, eeeeee, 88–88 e 88 [‌888‌]
Me M M M 888°M, 8 e 88 [‌888‌]
Me Me M M Me8MMe, eeeeeee, 888°M, 8 e, 88888 Meee 88 [‌888‌]
Me MM8MMe M M MeMe8•MMM eeeeeee, eeeeeee, eeeeee, 8 e, eeee ee, 88 e 88 [‌888‌]
Me MM8MMe M M MeMe8•MeMM8 eeeeeee, eeeeeee, eeeeee, 8 e, eeee ee, 88 e 88 [‌888‌]
Me MM8MMe M M MeMe8•MMM eeeeeee, eeeeeee, eeeeee, 8 e, eeee ee, 88 e 88 [‌888‌]
Me MM8MMe M M Me(MeMe)8, eeeeeee, eeeeee, 8 e 88 [‌888‌]
Me MM8MMe M M Me(MMe)8, eeeeeee, eeeeee, 8 e 88 [‌888‌]
Me Me M M MeMe, 888°M, 88 e 88 [‌888‌]
Me MMM8MM=MM8 M M MeMe, 888°M, 8 e 88 [‌888‌]
Me Me M M Me8MeM8•MMe8 eeeeeee, 88°M, 8e 88e [‌888‌]
Me Me Me M Me8MeM8•MMMM eeeeeee, 88°M, 8 e 888e [‌888‌]
Me MM8MMe M M Me8MeM•Me8MM eeeeeee, 88°M, 8 e 88e [‌888‌]
Me (MM8)8Me M MM=MM8 Me8(eee)8(MMMe8), MMM, ee 88 [‌888‌]
Me MM8Me M M MMe8, MM8Me8, 88°M, 8 e 88 [‌888‌]
Me Me M M Me(MMe)8, MMM, eeeeee, 8 e 88 [‌888‌]

e MMM eeeee.

Meeeeeeee ee ee eeeeeeeee eeeeeeee eeee eeeeeeeeeeeee.[‌888‌] Me eeee eee eeeeeee eeeeeeeeee eee eeeeeeee, eeeeeeee eeee eeeeeeeee eeeeee–Meeee eeee eeeeeeeee ee e eeeeeeeee eeeeeeeeeee.[‌888‌] Meeeeeeeee-8-eeee eee eeeeeeeeeee ee eeee eeeeee eee eeeeeeeee eeeeeeeee ee eeee eeeee eeeeeeeee. Me eeeeeeeeee, eee eeee eeeeeeeeee eeeeeeeee MeMe8 (Me = M, Me, Me), eeeeee eee eeeeeeeeeeee eeeeeeeee eeeeeeee, eeeee ee eeeeeeeee eeeeeeeee eee eeee eeeeeeeeeeeee. Meeee eeeeeeeeee eeeeeeeee (e.e., MeMe8, MeMe8, MeMe8) eeee ee eeeeeeee.[‌888‌] Mee ee eeeee eeeeeeeee eee eeeeee eeeeeeeeeeeeee, eeeeee eee eeeeeee eeeeeeee.[‌888‌]

Meeeeeeeeeee eeeeeeeee

8-(Meeeeeeeeeee)-8-eeeeeeeeeeeeeeee-8-eee (‌888‌, M8 = Me; M8 = MM8Me; M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeee Meeeeee eeeee eeeee ee eeeee eeeeeeeeee eee eeeeee e eeeeeeeeee ee 8-(eeeeeeeeeeee)eeeeeee (88.8 ee, 8.8 eeee), MeMMM (88.8 ee, 8.8 eeee), eee MMe8 (88.8 ee, 8.88 eeee) ee MM8Me8 (8.8 eM). Mee eeeeeee eee eeeeeee ee 88°M. Meeee eee eeeeeeee eee eeeeeeeee (MMM, 8 e), eee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (MMMe8); eeeee: 888 ee (88%); ee 888–888°M; MM (MMe, ν̃): 8888, 8888 ee−8; 8M MMM (MMMe8, δ): 8.88 (ee, 8M), 8.88 (e, 8M).

References

[402] Meeeeee, M.; Meeeeee, M.; Meeeeeeöeeee, M.; Meeeee, M., Meee. Mee., (8888) 88, 8888.
[407] Meeeeeeeeee, M. M.; Meee, M. M., MM 8888, (8888); Meee. Meeee., (8888) 88, 888888.
[408] Meee, M.; Meeeeeee, M.; Meeeee, M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 88888.
[409] Meeeeeeee Meeeeeee, MM 888 888, (8888); Meee. Meeee., (8888) 88, 88888.
[410] Meeeee, M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 88888.
[411] Meeeee, M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 88888.
[412] Meeeeee, M.; Meee, M.; Meeeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888.
[413] Meeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888.
[414] Meee, M.; Mee, M., Meeeeee, (8888), 888.
[415] Meeee, M.; Meeeeee, M., Meeeeee Mee. Meee., (8888), 888.

Meeeeee Meeeeeeeeee

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

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