Science of Synthesis

Cox, L. R., Science of Synthesis, (2008) 36, 118.

Ozonides (1,2,4-trioxolanes) are readily prepared from the action of ozone on alkenes. They can be reduced to alkanols in a variety of ways; thus a transformation involving alkene ozonolysis, followed by reduction of the intermediate ozonide (generally not isolated), provides a very useful two-step unmasking of an alkanol from the corresponding alkene (‌Scheme 61‌).

‌Meeeee 88‌ Meeeeeeee Meeeee ee ee Meeeee Meeeeeeeee Meeeeee Me Meeeeee Meeeeeee

Meeeeeee Meeee eeeeee eeeeeeeee eeeeeeeeeeeeee ee eeeeeeee eee eeee eeee ee eeeeeeee eeeeeee eeeeeeee ‌88‌ (‌Meeee 88‌, eeeee 8),[‌888‌] eeeeeee eeeeeeee eeeeee, ee eeeeeeeeee eeeeeee eeeeeeee eeeeeee,[‌888‌–‌888‌] eee eeee eeee eeeeee eeee eee eeeeeeee eee eeee eeeeeeeeeeeeee (eeeee 8). Me eeeeeeeeeeeeeeee eeeeee eeeee eeee eeeeeee eeeeeeee eeeeeee, eeeeee eeeeeeeeeee eeeeeeee e eeeeee eee eeee eeeeeeeee eeeeeeeeeee (eeeee 8).[‌888‌,‌888‌,‌888‌] Meeeeee eeeeeee eeee eeee eeee eeeeeeeeeeee, eeee eee eeeeee–eeeeeeee eeeeeee eeeeeee eeeeeee ee ee e eeeeeeeeeeee eeeeeeeee eeeeeee eee eeeeeeeee eeee eeeeeeee (eeeee 8).[‌888‌]

‌Meeee 88‌ Meeeeeeee Meeeeee ee eee Meeeeeeeee Meeeeeee eeee Meeeeeee Meeeeee Me Meeeeee Meeeeee Meeeeeee[‌888‌,‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

88-Meeeeeeeeeeeeee Meee [‌88‌, M8 = (MM8)8MM8M; ‌Meeee 88‌, Meeee 8]; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeee ee e eeeeee eeeeeeee ee eee eeee, eeeeee eeeeeeeee, eeeee, eee eeee. Meeeee eeeeeee eeeeee eeeeee eee eeeeeee eeeee ee eeeeeee eeee eeee eee eeee.

MMMMMMM: Meeee eeeeeeeee eeeeee eeeeeeeee eee eee eeeee eee ee eeeeee eeeeeeeee ee e eeeeee ee eeeee.

M8 eee eeeeeee eeeeeee e eeee ee eeeee-88-eeeee eeee (88.8 e, 8.88 eee) ee eee MeMM (88 eM) ee 8°M eeeee ee eeeeeee eeeee eeee eee eeeeeee ee eeeeee eeeeeeeeeee e eeeeee eeee ee Me8 ee eeeeeee MeMM. Mee eeeeeeeee eeeeeee eeee eee eeeee eeeeeeee ee ee eee-eeee eeee ee MeMM (88.8 e) eee MeMM8 (88.8 e, 8.88 eee) ee 88% ee MeMM (888 eM). Meeeee eeeeeeeee ee M8 eee eeeeeeee. Meeee 88 e, eee MeMM eee MeMM eeee eeeeeee ee eeeeeee eeeeeeee eeeeeeeeeeee (eeee eeeeeeeeeee <88°M). Mee eeeeeeeee eeeeeeee eeee eee eeeee eeeeeeee, eeee eeeeeeee, ee eee-eeee ee MMe (8.8 M) eee eee eeeeeeeeeeee eeee eeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee eee-eeee M8M, eee eeeee eeeee eeeeeee eeeeeeee; eeeee: 88.8 e (88%); ee 88°M.

Meeee-8-ee [‌88‌, M8 = (MM8)8Me; ‌Meeee 88‌, Meeee 8]; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeee eeeeeeeee eeeeee eeeeeeeee eee eee eeeee eee ee eeeeee eeeeeeeee ee e eeeeee ee eeeee.

M 888-eM, eeeee-eeeeee, eeeee-eeeeeeee eeeee eee eeeeeeee eeee e eee-eee eeee eeeeee eeeeeeeee eeeeeeeee ee e MeMe8 eeeeee eeee, ee M8 eeeee eeee, eee e eeeeeeee eeeeeee eeee. Mee eeeee eee eeeeeee eeee eee-8-eee (8.88 eM, 8.8 eeee) eee MM8Me8 (88 eM) eee eeee eeeeee ee −88°M. M8 eee eeeeeee eeeeeee eee eeee (eeee eeee ~88 eM·eee−8) eee 8 e ee eeeee eee eeee eeeee eeeeeeeeee ee eeeeeeeee M8 eee eeeeeee. Mee M8 eee eeeeeeee eeee M8, eeeee eee eeeeeee eeeeeee eee eeeee eee 88 eee ee eee eeeeeeeeeee ee eee eeeeee eee eeeeee ee ee. MMM (8.88 eM, 88 eeee) eee eeeee eeee eeeeeee eeeeeee eee eee eeeeeee eee eeeeeee ee eeeee eee 88–88 e. Meee, 8% ee MMe (8 eM) eee eeeee eee eee eeeeeeeee eeeeeee eee eeeeeee eee 8 e eee eeeeeeee eeeee eeeee MeMMM8. Mee eeeeeee eee eeeee (MeMM8) eee eeeeeeee, eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee; eeeee: 8.88 e (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.