A General Route to Terminally Substituted Allylic Derivatives of Silicon and Tin. Preparation of Allylic Lithium Reagents.
Abstract
It is obvious that this new route to allylic compounds of silicon and tin should be quite general in its scope of applicability. By appropriate variation of the phosphorus ylide and the carbonyl substrate in these reactions, allylic derivatives of silicon and tin of type Me3MCH2C(R)=CR'R'', where R, R' and R'' should be capable of wide variation, should be accessible. The allyltins thus prepared would provide starting materials for many new allylic lithium reagents. In many cases the direct lithiation procedure, the reaction of RLi/Lewis base or RLi/Me3OK with an appropriate unsaturated hydrocarbon, would provide the simplest route to the desired allylic lithium reagent. However, the additives which usually are required to effect such metalations may not always be compatible with other functionality in the carbonyl reactant or may interfere in other ways. Also, there will be instances when the appropriate unsaturated hydrocarbon is not available. Thus the versatility of our new procedure and its ease of application may prove very useful in organic and organometallic synthesis.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jun 01, 1977
- Accession Number
- ADA042884
Entities
People
- Dietmar Seyferth
- Karl R. Wursthorn
- Robert E. Mammarella
Organizations
- Massachusetts Institute of Technology