Β-lactone Formation Research Articles

Cyclic hydroxycarboxylic acids. I. Synthesis, stereochemistry and reactivity of 2,3-trans-2,3-Dihydroxycyclopentanecarboxylic acids

Cyclopent-2-enecarboxylic acid and performic acid give a mixture of approximately equal amounts of the corresponding c-2,t-3- and t-2,c-3-dihydroxycyclopentane-r-1-carboxylic acids. The mixture was separated by chromatography of the methyl esters. Relative configurations were assigned from the action of tosyl chloride-pyridine on the separate acids. The c-2,t-3-dihydroxy acid yields a t-3-tosyloxy ,β-lactone and the t-2,c-3-dihydroxy acid yields a r-2-tosyloxy γ-lactone. Structures of the lactones were proved by correlating the products of acidic methanolysis and of alkaline hydrolysis with various derivatives of the acids. Proton magnetic resonance spectra are reported for 21 compounds from the two stereochemical families, including acetate, trifluoroacetate, tosylate and mesylate derivatives. Infrared data for relded lactones are tabulated. Formation of β-lactones from β-hydroxy acids by tosyl chloride appears to be unprecedented.

Formation of β-lactones in the iodolactonization reaction

Formation of β-lactones in the iodolactonization reaction

β-Lactone formation in a halogeno-lactonization reaction

The first example of β-lactone formation resulting from halogeno-lactonization of a βγ-unsturated acid is reported.

Walden Inversion in the Formation of β-Lactones. The Configurations of the Bromo-acids of Kohler and Jansen

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTWalden Inversion in the Formation of β-Lactones. The Configurations of the Bromo-acids of Kohler and JansenPaul D. Bartlett and Paul N. RylanderCite this: J. Am. Chem. Soc. 1951, 73, 9, 4275–4280Publication Date (Print):September 1, 1951Publication History Published online1 May 2002Published inissue 1 September 1951https://doi.org/10.1021/ja01153a073RIGHTS & PERMISSIONSArticle Views60Altmetric-Citations11LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (677 KB) Get e-Alerts Get e-Alerts

161. —Investigation on the formation and stability of β-lactones

161. —Investigation on the formation and stability of β-lactones