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

Abstract

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.