ISSN:
0009-2940
Keywords:
Ethylenes, 1,1-diactivate
;
Michael acceptors
;
1-Oxa-1,3-butadienes
;
Hetero Diels-Alder reaction
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19911241118
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