Science of Synthesis

Harrison-Marchand, A.; Chataigner, I.; Maddaluno, J., Science of Synthesis, (2005) 26, 1248.

Pinacol rearrangement of tetrasubstituted glycols offers an interesting route to α-trisubstituted ketones, but unsymmetrical substrates often lead to mixtures of regioisomers since the hydroxy groups cannot be discriminated in most cases. However, this rearrangement is useful for glycols bearing a methylsulfenyl group.[‌247‌]

Me eee eeeeeeeeee eeeeee, eeeeeeeeeee eeeeeeeeeeeeee ee 8,8-eeeee eeeeeeee, e.e. ‌88‌, eeeeeeee e eeeee ee β-eeeeeee eeeeeee eeee ee ‌88‌ ee ‌88‌ (‌Meeeee 88‌).[‌888‌–‌888‌] Meeeeeee eeeee ee e β-eeeeeeeeeee ee eee eeeeeee, eee eeeeeeeeeeeee eeeee ee α,α-eeeeeeeeeeeee β-eeeeeee eeeeeee, eee eeeeee eeeeeeeeee ee eeeeeeeeeeee eeeee eeeeeeeee.[‌888‌–‌888‌] Me eeee eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee, eeee eee- ee eeee-eeeeeeee eeeeeeeee eeeeeee ee eee- ee eeee-β-eeeeeee eeeeeee eeeeeeeeeeee;[‌888‌–‌888‌,‌888‌–‌888‌] eeeeeee, eee- eee/ee eeee-eeeeeeee eee eeee eeee ee e eeeeee eee-eeeeeeeeeeee.[‌888‌,‌888‌] Me eeeeeee, eee eeeeeeeee eeeeeeee eeee eee eeeeeee eeee eeeeeeeeeeeee eeeeeee eee eee eeeeeee ee eeeeeeeeee ee eeeeeeee ee eee eeeeeee M—M eeee ee eeeeeeeeeeee ee eee eeeeeee eeeeee ee eee Meeee eeee eee 8,8-eeeeeeeee eeeeeeeeeee eeee M—M eeeeeeee ee e eeeeeeeeee-eeeee eeeeeeee eeeeeeeeee eeeeee eeeeeeeeeeee eeeeeeeeeeee (eeee eeeeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee). M eeeeeeeee eeeeeeeeeee ee eee eeeeeeeee eeeee eee eee eeeeeeeee eeeeee eeeee eeeee eeeeeeeee ee eeeeeeee eee eeee eee eeee eeeeeee eee eeeeeeeeeeeeeeeee eeeeeeee ee eeeee eeeeeeeee.[‌888‌–‌888‌]

Meeeeeeee, eeeeeeeeeeeeee eeeeeee ee Meeee eeeee eeee eeeeeee, eeeeeeeee eee eee ee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee, eeeee eeeeeeeeeeeeeeeeeeeeeeeee, ee eeee ee eeeeeeee- eee eee-eeeee Meeee eeeee;[‌888‌–‌888‌] eeeeeee, eeee- eee eeeeeeeee-eeeee Meeee eeeee, ee eeee ee eeeeeeeeeee, eeee eeee eeee ee eeeeeeeee eeeeeee.[‌888‌–‌888‌] Mee eeeeeee eeeeee ee ee eeeeee eeeeeeeee eeeeeeeee eee eeeeeeeee ee ee eeeeeeeeee ee eeeeeee e eeeeee Meeee eeee eee eeee eeeeeeee. Meeeeeeeeeeeeeeeeee, eeeee, eeeeeee, eeeeeeeeeee, eee eeee eeeeee eeeeeee eeeeeeeee eeeeeeeee, eee eeeeee eeeeeeeeee eeee eeeee eeeeee eeeeeee ee eeeee eeeeeeeee. Me eeee eeeeeeeee eeeee, ee eee ee eeeeeeeee ee eeeeeee eee eeeeeee eeeee ee e eeeeeeeeeeeeee eeeee[‌888‌,‌888‌,‌888‌,‌888‌] ee eeeeeee[‌888‌] eeeee. Meee eeee ee eeeeeeeeeeeee eee eeee eeeeeee ee e eee eeee ee eee eeeee eeeeeeeee ee e eeeeeeeee.[‌888‌]

Me eeeeeee eeeeeeeeeeeeee, eee eee-eee eeeeeeeee ee α-eeeeeeeee eeeeeee eeeeeeee[‌888‌] eeeeeeee eeeee ee α-eeeeeeeee β-eeeeeee eeeeeee. Me eeeeeeee, eee eeee-eeeeeeeee eeeeeeeeeeeeee ee eeeeeeeeeeeeeee[‌888‌] ee eeeeeeee[‌888‌–‌888‌] eeeee β-eeeeeee ee β-eeeeee eeeeeee.

‌Meeeee 88‌ Meeeeee-Meee Meeeeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M)-8-Meeeeee-8,8-eeeeeeeeeeeeee-8-eee (‌88‌, M8 = Me; M8 = Me):[‌888‌]

Me e eeee ee eeeeeee ‌88‌ (888 ee, 8.88 eeee) ee eeeee MM8Me8 (8 eM) eee eeeee Me(MMe)8 (888 ee, 8.888 eeee) eee eee eeeeeee eee eeeeeee ee ee eee 8 e. M8M (88 eM) eee eeeee eee eee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (MeMM8) eee eee eeeeeee eee eeeeeee ee eeeee ee eeeeeee eeeeee eeeeeeee; eeeee: 888 ee (88%).

References

Meeeeee Meeeeeeeeee

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