The Malonic Ester Synthesis with Styrene Oxide and with Butadiene Oxide

Citation data:

Journal of the American Chemical Society, ISSN: 1520-5126, Vol: 69, Issue: 1, Page: 11-13

Publication Year:
1947
Usage 15
Abstract Views 15
Citations 28
Citation Indexes 28
Repository URL:
http://scholarsmine.mst.edu/chem_facwork/1538
DOI:
10.1021/ja01193a003
Author(s):
Russell, Robert R.; VanderWerf, Calvin Anthony
Publisher(s):
American Chemical Society (ACS)
Tags:
Chemical Engineering; Chemistry; Biochemistry, Genetics and Molecular Biology
article description
1. The condensation of styrene oxide and of butadiene oxide with sodium malonic ester, followed in each case by hydrolysis and decarboxylation, has been found to yield γ-phenyl-γ-butyrolactone and γ-vinyl-γ-butyrolactone, respectively. The fact that no other lactone could be isolated in either case indicates that the attack of the nucleophilic anion of malonic ester occurs exclusively at the terminal (unsubstituted) carbon atom of the epoxide ring. 2. On the basis of the direction of epoxide ring opening in the reaction of styrene oxide and of butadiene oxide with sodium malonic ester, the generalization that the phenyl and vinyl groups always exhibit a —I effect as compared with the hydrogen atom, appears unjustified. © 1947, American Chemical Society. All rights reserved.