0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via Variation 1: Alkanoic Acid Derivatives by the Arndt–Eistert Chain Elongation

DOI: 10.1055/sos-SD-023-00535

Tidwell, T. T.Science of Synthesis, (200623592.

The ArndtEistert reaction involves Wolff rearrangement in the presence of nucleophilic solvents to form ketenes that are captured by the solvent, and it provides a method for chain elongation of carboxylic acids by one carbon;[‌100‌] further information on this reaction can be found in HoubenWeyl, Vol. 10/4, p 473. The preparation of equilenin, an early landmark in total synthesis, involves the Wolff rearrangement of the diazo ketone 134 to give the ketene 135 that is captured by methanol to form the intermediate 136, which is used in the synthesis of equilenin (Scheme 42).[‌101‌]

Meeeee 88 Mee MeeeeMeeeeee Meeeeeee ee eee Meeee Meeeeeeee ee Meeeeeeee[‌888‌]

Meeeeeee ee eeeee eeeeee 888 ee eeee eeeeee 888 eeeee (8,8-eeeeeeeeeeeeeeeee-8-eeee)eeeeee eeee (888) ee 88% eeeeeee eeeee eeee eee eeee eeeeeeee eeeeeeeee: eee eeeeeee 888 ee e eee eeeeeeeeeeee eee eee eeeeeeeeeee ee e eeeeeeeee eeee ee eee eeeee ee eee eeeeeeeee ee e eeeeeeeeeeeee eeeeeeeeeee ee eeee e eeeeeeeeeeeeeee[8.8.8]eeeeeee eeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 (8,8-Meeeeeeeeeeeeeeee-8-eeee)eeeeee Meee ee MeeeeMeeeeee Meeee Meeeeeeeee[‌888‌]

Me MeeeeMeeeeee eeeeeeee ee eee eeeeeeeee ee eee MM eeeeeeeee MM-888,888 eee MM-888,888 ee eeeeeeee ee ee eeeeeeeee eeeeeee eeeeeeee eeeeeeee ee eeeee eee eeeee eeeeee 888, eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee eeee eee eeeeeeeeeeeeeeee ee eee eeeeeeeee eeee, ee e eeeeeeeee eeeeeeee ee eeeeeee ee eeee eeeeeeeeee eeeeeeeee eeeeeeeee.[‌888‌] Meeeeeeeeee ee eee eeeeeeee ee 8 eeeeeeeeeee ee eeeeeee eeeeeeee eeeeee(MM) eeeee ee eeeeeeeeeeeeeeeee/eeeee (8:8) eeeee eee eeeeee 888, eeeee eeeee ee eee eeeeeeeeeee eeeee 888 ee 88% eeeee eeee eee eeeeeeeee eeeeeeeeee eeee (Meeeee 88).[‌888‌]

Meeeee 88 MeeeeMeeeeee Meeeeeeee ee e MM Meeeeeee Meeeeeeeeeee[‌888‌]