On heating the furan endoperoxide (2) rearranges into the enol ester (4) and the bicyclic ozonide (3) affords instead the rearranged ozonide (7). The process (2) → (4) represents an intramolecular Baeyer-Villiger rearrangement presumably via the dioxirane (D-2), while the process (3) → (7) represents intramolecular trapping of the carbonyl oxide (C-3).
Tetraphenylporphyrin-sensitized photooxygenation of 2-methyl-5-trimethylsilylfuran (4) affords quantitatively trimethylsilyl 2-oxo-4-pentenoate (5), presumably via intramolecular Baeyer-Villiger rearrangement of the intermediary dioxirane (3a).
AbstractAus Bis‐trimethylsilyl‐peroxid (I) erhält man mit Schwefeltrioxid das Persulfat (II), das in Baeyer‐Villiger‐Reaktionen eingesetzt werden kann.
AbstractDie Furan‐endoperoxide (I)‐(III) (hergestellt durch Photooxidation der entsprechenden Furanderivate in Gegenwart von Tetraphenylporphyrin als Sensibilisator) oxidieren in CFCl3 Tetramethylethylen zum Epoxid und Diphenylsulfid zum Sulfoxid, an.
AbstractFurane (I) w den mit Singlet‐Sauerstoff in Methylenchlorid bei ‐78°C zu Trioxabicycloheptenen (II) umgesetzt, die nach Reduktion mit Diimin als Trioxabicycloheptan (III) isolie werden können.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTBis(trimethylsilyl) monoperoxysulfate: convenient Bayer-Villiger oxidantWaldemar Adam and Augusto RodriguezCite this: J. Org. Chem. 1979, 44, 26, 4969–4970Publication Date (Print):December 1, 1979Publication History Published online1 May 2002Published inissue 1 December 1979https://pubs.acs.org/doi/10.1021/jo00394a048https://doi.org/10.1021/jo00394a048research-articleACS PublicationsRequest reuse permissionsArticle Views342Altmetric-Citations31LEARN 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 InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCyclic peroxides. 60. Prostanoid endoperoxide model compounds: preparation of 1,2-dioxolanes from cyclopropanesWaldemar Adam, Arnoldo Birke, Carlos Cadiz, Simon Diaz, and Augusto RodriguezCite this: J. Org. Chem. 1978, 43, 6, 1154–1158Publication Date (Print):March 1, 1978Publication History Published online1 May 2002Published inissue 1 March 1978https://pubs.acs.org/doi/10.1021/jo00400a028https://doi.org/10.1021/jo00400a028research-articleACS PublicationsRequest reuse permissionsArticle Views207Altmetric-Citations23LEARN 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 InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts