The Reaction of some Carbonyl and Thiocarbonyl Compounds with Prenyl- and Crotyllithium in Tetrahydrofuran Solution

✍ Scribed by V. Rautenstrauch

• Publisher: John Wiley and Sons
• Year: 1974
• Tongue: German
• Weight: 825 KB
• Volume: 57
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19740570226

✦ Synopsis

Abstract

Prenyllithium (3‐methylbut‐2‐enyl‐lithium) (1) and cis‐crotyllithium (Z‐but‐2‐enyl‐lithium) (2) in tetrahydrofuran solution, prepared according to the method of Eisch & Jacobs, react with carbonyl compounds to give the branched alcoholates with moderate to high selectivity, unless access to the carbonyl group is strongly hindered (see the Table). Adamantanethione (12) reacts with 1 to give the unbranched thiolate.