Addition of thallium triacetate to PFG methyl ester and related compounds in acetic acid. Nuclear magnetic resonance spectral study of novel dioxatricyclic and oxabicyclic products

Vilmos Simonidesz, Ágnes Behr-Papp, József Ivanics, Gábor Kovács, Eszter Baitz-Gá, Lajos Radics

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6 Citations (Scopus)

Abstract

Addition of Tl(OAc)3 in acetic acid to prostaglandin F methyl ester (1) and its congeners (4) and (5) gave, with participation of 9-OH, the bicyclic enol ethers (26) which reacted in situ with a further equivalent of Tl(OAc)3 to yield as the main products the dioxatricyclononane derivatives (2), (6), and (9) and (3), (7), and (10), respectively. Elucidation of the structure of the products by 1H and 13C n.m.r. is presented and a mechanism of the transformations based on model studies is proposed.

Original languageEnglish
Pages (from-to)2572-2580
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
Publication statusPublished - Jan 1 1980

ASJC Scopus subject areas

  • Chemistry(all)

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