Module 2 : Reduction Reactions

Lecture 16 : Dissolving Metal Reductions (Na-Liq. NH3, Li-Liq. NH3, etc.)

 

Examples:

A. G. Schultz, L. Pettus, J. Org. Chem. 1997, 62, 6855.

E. J. Corey, N. W. Boaz, Tetrahedron Lett. 1985, 26, 6015.

A. Gopalan, P. Mangus, J. Am. Chem. Soc. 1980, 102, 1756.

 

2.2.5 Reduction of Alkynes

The reduction of alkynes to trans alkenes selectively is carried out by the dissolved metal in ammonia. This reaction specifically gives the trans alkenes (E alkenes) where as the reduction with Lindlar catalyst gives the cis alkenes (Z alkenes) (Scheme 8). 

Scheme 8

Proposed Mechanism for Lindlar Reduction