Dieckmann Condensation

Schematic representation of the Dieckmann Condensation.

Mechanism of the Dieckmann Condensation

Mechanism of the Dieckmann Condensation

Original publication	Ber. Dtsch. Chem. Ges.. 1894, 27, 102. Synthesis. 1983, 1983, 996.
Reviews	Comp. Org. Syn.. 1991, 2, 806. Org. React.. 1967, 15, 1.

Sample reactions

intermediate structure

NaOMe

MeOH

Reflux, 20 min, 88%

intermediate structure

intermediate structure

i-Pr2NLi

THF

-78 °C, 40 min, 84%

intermediate structure

intermediate structure

KOt-Bu

Et2O

0 °C, 3 h

intermediate structure

intermediate structure

intermediate structure

i-Pr2NLi

THF

-78 °C to RT, 3 h, 64-85%

intermediate structure

intermediate structure

TBSCl, TMS2NLi

Hexane(s), HMPA, THF

Reflux, 2.5 h

intermediate structure

intermediate structure

NaH

MeOH, PhMe

Reflux

intermediate structure

intermediate structure

NaOMe

PhMe

Reflux, , 33%

intermediate structure

intermediate structure

NaH, (CO2Me)2

DMF, MeOH

35-80 °C, , 44%

intermediate structure

intermediate structure

NaH

DMF, MeOH

RT to 155 °C, 20 min

intermediate structure

intermediate structure

H2O, HCl, KOt-Bu

PhMe, t-BuOH

0 °C to Reflux, ON, 100%

intermediate structure