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Sterically Hindered Double‐Bond Systems, VII [1l] . On the Reaction of Succinic Esters with tert ‐Butyllithium
Author(s) -
Hopf Henning,
Hänel Ralf
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.1491271137
Subject(s) - chemistry , steric effects , yield (engineering) , butyllithium , double bond , medicinal chemistry , succinic acid , organic chemistry , materials science , metallurgy
Addition of tert ‐butyllithium to dimethyl ( 1a ) and diethyl succinate ( 1b ), respectively, provides 2,2,7,7‐tetramethyl‐3,6‐octanedione ( 3 ) in good yield as well as the ketoesters 5a/b and the cyclized products 6 and 7. The mode of formation of these latter side products is discussed, and several published errors concerning these transformations are corrected.