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Preparation and Selected Reactions of t ‐Butyl 2‐Methylene‐3‐oxoalkanoates
Author(s) -
Martin H.,
Hoffmann R.,
Gassner Andreas,
Eggert Ulrike
Publication year - 1991
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.19911241118
Subject(s) - chemistry , dabco , methylene , enol , steric effects , medicinal chemistry , alkyl , catalysis , organic chemistry , polymer chemistry
The title class of 1,1‐diactivated ethylenes has been prepared in two steps from aldehydes and t‐ butyl acrylate by (i) DABCO‐catalyzed coupling to give t ‐butyl 2‐(hydroxyalkyl)‐2‐propenoates 11 and (ii) low‐temperature Jones oxidation, followed by swift work up at low temperature. The resulting t ‐butyl 2‐methylene‐3‐oxoalkanoates 12 are stabilized by sterically demanding and also by aromatic groups R. For primary unhindered alkyl groups, stability is low. The compounds enter into Michael reactions, hetero Diels‐Alder additions with enol ethers, and self‐dimerization.