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The Reaction of some Carbonyl and Thiocarbonyl Compounds with Prenyl‐ and Crotyllithium in Tetrahydrofuran Solution
Author(s) -
Rautenstrauch V.
Publication year - 1974
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19740570226
Subject(s) - chemistry , tetrahydrofuran , lithium (medication) , prenylation , selectivity , medicinal chemistry , carbonyl group , organic chemistry , catalysis , medicine , solvent , enzyme , endocrinology
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.