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, E. Gács-Baitz, Lajos Radics

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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
Publication statusPublished - 1980

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Ethers
Thallium
Prostaglandins F
Acetic Acid
Esters
Nuclear magnetic resonance
Derivatives

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Addition of thallium triacetate to PFG2α methyl ester and related compounds in acetic acid. Nuclear magnetic resonance spectral study of novel dioxatricyclic and oxabicyclic products",
abstract = "Addition of Tl(OAc)3 in acetic acid to prostaglandin F 2α 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.",
author = "Vilmos Simonidesz and {\'A}gnes Behr-Papp and J{\'o}zsef Ivanics and G{\'a}bor Kov{\'a}cs and E. G{\'a}cs-Baitz and Lajos Radics",
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journal = "Journal of the Chemical Society, Perkin Transactions 1",
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T1 - Addition of thallium triacetate to PFG2α methyl ester and related compounds in acetic acid. Nuclear magnetic resonance spectral study of novel dioxatricyclic and oxabicyclic products

AU - Simonidesz, Vilmos

AU - Behr-Papp, Ágnes

AU - Ivanics, József

AU - Kovács, Gábor

AU - Gács-Baitz, E.

AU - Radics, Lajos

PY - 1980

Y1 - 1980

N2 - Addition of Tl(OAc)3 in acetic acid to prostaglandin F 2α 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.

AB - Addition of Tl(OAc)3 in acetic acid to prostaglandin F 2α 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.

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