Science of Synthesis

Podlech, J., Science of Synthesis, (2007) 25, 46.

Sulfoxides can be rearranged into O,S-acetals by treatment with an anhydride (Pummerer rearrangement), and can then be hydrolyzed to aldehydes.[‌153‌,‌154‌] Hydrolysis of the acetals is achieved with either sodium hydrogen carbonate, copper(II) chloride, or mercury(II) chloride.[‌155‌,‌156‌] ‌Scheme 23‌ shows three aldehydes ‌34‌ that are obtained by treating the corresponding sulfoxides ‌33‌ with trifluoroacetic anhydride in acetonitrile containing a base, such as 2,6-lutidine, at room temperature, and hydrolyzing the product directly with aqueous sodium hydrogen carbonate.[‌155‌]

‌Meeeee 88‌ Meeeeeeee eee Meeeeeee Meeeeeeeeeeeee ee Meeee Meeeee Meeeeeeeee[‌888‌]

Meeeee eeeeeeee eee eeee ee eeeeeeeeeee eeee eeeeeeeee ee eeeeeeeee eeee eeeeeeee eeeeeeee, eee eeee eeeeeee eee eeeeeee eeeeeee eee eeeeee eee. Meeeeee, eeeeeeee eeeeee ee eee eeeeee 88%, eee eeeeeee eeeee eee eeeeeeeee ee ee. 88% ee eee M,M-eeeeeeee eeeeeeeeeeee ee e eeeeeeeee.[‌888‌] Meeeeeeeeeeee, eeeeeeee eee ee α-eeeeeeeeeee eeee M-eeeeeeeeeeeeeeeee eee eeeeeeeeeeee eeeeeeeeee eeee eeeeee eeeeee[‌888‌] ee eeeeeee eeeee.[‌888‌] Me eeeeeee ee eeeeeeee ee eee eeeeeeeeeee ee eeeeeeee ‌88‌ ee eeeeeeeee ee eeeeeee ‌88‌ eeeee M-eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeeeeee, eee eeee eeeeeeeee ee eee eeeeeee ee eeee eeee eeeeee(MM) eeeee eee eeeeee(MM) eeeeeeee ee eeeeeee eeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeee Meeeeeeee ee Meeeeeeee ee ee Meeee Meeeee Meeeeee[‌888‌]

Meeeeeeeeeeee ee eeeee eeeeee eeeeeee eeee eeeeeeeeeeee eee eeeeeeeeee eeeeeeeee eeee eee(eeeeeeeeeeeeee) eeeeeeee eeeee ee eeeeeee ee 88% eeeee (‌Meeeee 88‌); eeee eeeeee eeeee ee eeee eee eeeeeee ee eee, ee eee ee eeeeeee eeee eeee eeeeee eee ee eeeeeee ee eeeee eeeeee eeeeeeee eeeeeee e eeeeeee eeeee eeeee.[‌888‌] Me e eeeeeee, eee eeeee eeeeeeee, eeeeeeeee eeeeee eeeeee eeeeeee eee ee α-eeeeeeeee eee eeeeeeeee ee eeeeeee–eeeee eeeeeeee, eeeeeeee ee eeeeeeeee eee eeeeeeeeeee; ee eeee eeee eee eeeeeee eeeeeeee ee eeeeeeee ee 88% eeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeeeee ee Meeee Meeeee Meeeeeee eeee Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

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

MMMM (88 eeee) ee MeMM (88 eM) eee eeeee ee e eeee ee eeeee eeeeee eeeeeeeee (8.88 e, 88 eeee) eee 8,8-eeeeeeee (88 eeee) ee MeMM (88 eM) eeee ee 8°M eeeee M8, eee eeee eee eeeeeee eee eeeeeee ee eeee eeeeeeeeeee eee 88 eee. MeMMM8 (88 eeee) ee M8M (888 eM) eee eeeee eee eee eeeeeeeeeee ee eee eeeeeee eee eeeeeee ee eeee ee ee. Meeee eeeeeeee eee eeeeeee eee 8 e, ee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeeee eeee eeeeee eeee eee MMe eee eeee ee MeMMM8, eee eeee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeeee eee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee), eee eeeeeeeee eeeee eeeeeee eeeeeeee (ee 88°M/88 Meee); eeeee: 8.88 e (88%); eeeeee >88%.

8-(8-Meeeeee-8-eeeeeeeeeeee)-8-eeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeee ‌88‌ (88 e, 88.8 eeee) ee eeeee MMe8 (88 eM) (MMMMMMM: eeeee) eee eeeee ee e eeee ee MMM (8.88 e, 88.8 eeee) ee eeeee MMe8 (888 eM) eee eee eeeeeee eee eeeeeee eee 8 e eeeee M8 ee ee. Meeee eeeeeeeeee, eee eeeeeee eee eeeeeee eeee eee eeeeeeee eeeee eeeeeee eeeeeeee. MeM (88.8 e), MeMe8•8M8M (88.8 e), eeeeeee (888 eM), eee M8M (8 eM) eeee eeeee ee eee eeeeeee, eee eee eeeeeee eee eeeeeeee eee 88 eee, eeeeee, eeeeeee eeee Me8M (888 eM), eee eeeeeeee. Mee eeeeeeee eee eeeeee eeee M8M (8 × 888 eM) eee eeeee (8 × 888 eM), eeeee (MeMM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee; eeeee: 8.88 e (88%). Meeeeeeeeeee ee ee eeeeeeeeee eeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/MM8Me8 8:88).

References

Meeeeee Meeeeeeeeee

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