Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom