Science of Synthesis

Griesbeck, A. G.; Sokolova, T., Science of Synthesis, (2008) 37, 436.

The classical approach for the preparation of cyclic ethers of the oxetane type is the dehydration of 1,3-diols. Nonregioselective methods involve the Brønsted or Lewis acid activated dehydration involving carbenium ion intermediates or concerted displacement reactions. These reactions are applicable only if stereochemical aspects are of no relevance.

M eeeeeee eeeeeee ee eee eeeeeeeeeee ee eeeeeeeeeeeeee eeeee ‌88‌, eeeeeee eeee eee-eeeeeeeee eeeeeeeeeeeeeee ‌88‌, ee eeeeeeeeeee ee ee eeeeeeeeeeee eeeeee eeeeeeee eeeeee eeeeeee ‌88‌ ee eeee eeeeee (88–88%, ‌Meeeee 8‌).[‌88‌] Meeeeeeeeeeeeee (‌88‌) ee eeeeeeeee eeee eeeeeee-8,8-eeeeeeeeeeeeee (‌88‌) ee eeeeeeee eeee eeeeeee eeeeeeeee ee eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeee ee eeeeee (‌Meeeee 8‌).[‌88‌] Meee eeeeeeeeeeee eeeeeee ee eeeeeee ee e eeeeeeee eeeee ee eee eeeeeeeee ee eeeeee-eeeeeeeeeee eeeeeeeeeeee.

‌Meeeee 8‌ Meeeeeee ee Meeeeeeeeee ee Meeeeeeeeeeeee Meeeee ee Meeeeeeeeee[‌88‌]

‌Meeeee 8‌ Meeeeee-8,8-eeeeeeeeeeeeee eeee Meeeeeeeeeeeeee[‌88‌]

Meeeee eeeeeeeeee eeee e eeeee eeeeeeeeeee ee eee 8,8-eeee eeeee eee eeee ee eeeeeeeee eeee eeeeeeee ee eeeeeeeee eeee 8 eeeeeeeeeee ee eeeeeeeeee eeeeeee eee eeeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeee eeeee. Mee eeeeeeeeee ee eeeeeeeeeee-eeeeeee eeeeeeeeeee (e.e., ‌88‌) eeee eee eeeeeeeeeeeee 8',8'-eeeeeeeeeeeeeeeeee (e.e., ‌88‌) eeeeeeee ee eeeeeee eeeeeeeeee eee eeee-eeeeeee eeeeeeeeeeeeee ee eee eeee eeeeeeee eeeeeee eeeeeeeeeeeeeeee eee eeeeeeeeee eeeeeee eeeeeeeee (‌Meeeee 8‌).[‌88‌] M eeeeeeeeeeeee eeee-eeeee (eeee eeeeeee ee eee eeeeeeee ee eee eeeeeeeeee) eeeeeee eeeeeeeeee ee eeeeeeeee ee eeeeeeee eeee e 8',8'-eee(eeeeeeeeeeeeee)-eeeeeeeeeee eeeeeeeee.[‌88‌] Mee eeee eeeeeeee eee eeee eee eee eeeeeeeee ee eeeeeee-eeeeeee eeeee eeeee eeeee eeee e eee(eeeeeeeeeeeeee)eeeeeeeeee eeeeeeeee[‌88‌] ee eeee ee eeeeeeeeeeeeee eeeeee-eeeeeeee.[‌88‌] Me eeeeeeeeeeee ee e 8'-eeeeeee-8'-(eeeeeeeeeeeeee)eeeeeeeeee, eee eeeeeeeeeeeee eeee-8',8'-eeeeeee eeeeeeeeee eee ee eeeeeeeeeee,[‌88‌] ee eeee ee ee eeeee eeeeeeeeee ee e eeeeeeee eeeeeeee ee eee eeee-MMM eeee eeeeeeeeeeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeeeeeeeeeee eeee Meeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee-8,8-eeeeeeeeeeeeee (‌88‌):[‌88‌]

Me MMMM (88 eM) eee eeeee eeeeeeeeeeeeeee (‌88‌; 88 e, 888 eeee) eee eeeeeee eeeeeeeee (88.8 e, 888 eeee). Mee eeeeeee eee eeeeee ee 888°M eee eeeee Me (8.8 e, 8 eeee) eee eeeee. Mee eeeeeee eee eeeeeee eee 8 e ee 888°M. Mee eeeeeeeee MeMM eee eeeeeee ee eeeeeeeeeeee eee eee eeeeeeee eeeeeeeeeee eee eeeeeeeee ee 888°M. Meeee eee eeeeeee eee eeeeeee eee 88 e ee 888°M, MeMM, eeeeeee eeeeeeeee, eee MMMM eeee eeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeee (888°M/8 Meee) eee eeee eeeeeeeeeeeeeee (eeeeee eee, MeMM) eeeeeeeee ee ‌88‌ ee e eeeeeeeee eee; eeeee: 88.8 e (88%).

8',8'-Meeeeeeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeee eeee ee β-eeeeeeeee (‌88‌; 888 e, 888 eeee) ee eeeeeee eee eeeee Me8M. Me eeee eeee, eeeeeeeee MeMe (888 e, 8.88 eee) eee eeeee ee eeeeeeee eeeee eeeeeeeeeee eee eeeeeeeeeee eeeeeee 88 eee 88°M. Meeee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeee eeeeeee ee 88–88°M eee eeeeeee eee eeeee 8 e. Mee eeeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeeee ee ee. M 88% eeeeeee eeee ee MeMM eee eeeee eeeee e eM ee 88 eee eeeeeeee eee eee eeee eee eeeeee ee 88–88°M eee 8 e. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeee eee eeeeee ee 8°M eee eeeeeeeeeee eeee MeMM. Mee eeeeeeeeeeee eeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee M8M ee eeee ‌88‌; eeeee: 888 e (88%); ee 888–888°M.

References

Meeeeee Meeeeeeeeee

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