The reaction between phloroglucinol and vic polycarbonyl compounds: extension and mechanistic elucidation of Kim's synthesis for bipolarofacial bowl-shaped compounds

Joseph Almog; Rinat Rozin; Asne Klein; Genyia Shamuilov-Levinton; Shmuel Cohen

doi:10.1016/j.tet.2009.07.056

The reaction between phloroglucinol and vic polycarbonyl compounds: extension and mechanistic elucidation of Kim's synthesis for bipolarofacial bowl-shaped compounds

Joseph Almog^*
, Rinat Rozin
, Asne Klein
, Genyia Shamuilov-Levinton
, Shmuel Cohen

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

Kim's serendipitous synthesis of a novel cavitand by the one-pot reaction between phloroglucinol and ninhydrin was revisited and extended. A much deeper cavitand was obtained by replacing ninhydrin with benzo[f]ninhydrin. Performing the reaction in a stepwise manner, employing both ninhydrin and benzo[f]ninhydrin, provided 'mixed bowls' of lower symmetry. Other cyclic polyketones, such as 1,2-indanedione and alloxan, form with phloroglucinol only partially closed structures. Crystallographic studies of the intermediate compounds in this reaction confirm Kim's postulate that the bowl formation involves hemiketal ring-openings and rearrangements.

Original language	English
Pages (from-to)	7954-7962
Number of pages	9
Journal	Tetrahedron
Volume	65
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2009.07.056
State	Published - 19 Sep 2009

Keywords

Bowl-shaped compounds
Hemiketals
Ninhydrin
Phloroglucinol

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10.1016/j.tet.2009.07.056

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title = "The reaction between phloroglucinol and vic polycarbonyl compounds: extension and mechanistic elucidation of Kim's synthesis for bipolarofacial bowl-shaped compounds",

abstract = "Kim's serendipitous synthesis of a novel cavitand by the one-pot reaction between phloroglucinol and ninhydrin was revisited and extended. A much deeper cavitand was obtained by replacing ninhydrin with benzo[f]ninhydrin. Performing the reaction in a stepwise manner, employing both ninhydrin and benzo[f]ninhydrin, provided 'mixed bowls' of lower symmetry. Other cyclic polyketones, such as 1,2-indanedione and alloxan, form with phloroglucinol only partially closed structures. Crystallographic studies of the intermediate compounds in this reaction confirm Kim's postulate that the bowl formation involves hemiketal ring-openings and rearrangements.",

keywords = "Bowl-shaped compounds, Hemiketals, Ninhydrin, Phloroglucinol",

author = "Joseph Almog and Rinat Rozin and Asne Klein and Genyia Shamuilov-Levinton and Shmuel Cohen",

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doi = "10.1016/j.tet.2009.07.056",

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T2 - extension and mechanistic elucidation of Kim's synthesis for bipolarofacial bowl-shaped compounds

AU - Almog, Joseph

AU - Rozin, Rinat

AU - Klein, Asne

AU - Shamuilov-Levinton, Genyia

AU - Cohen, Shmuel

PY - 2009/9/19

Y1 - 2009/9/19

N2 - Kim's serendipitous synthesis of a novel cavitand by the one-pot reaction between phloroglucinol and ninhydrin was revisited and extended. A much deeper cavitand was obtained by replacing ninhydrin with benzo[f]ninhydrin. Performing the reaction in a stepwise manner, employing both ninhydrin and benzo[f]ninhydrin, provided 'mixed bowls' of lower symmetry. Other cyclic polyketones, such as 1,2-indanedione and alloxan, form with phloroglucinol only partially closed structures. Crystallographic studies of the intermediate compounds in this reaction confirm Kim's postulate that the bowl formation involves hemiketal ring-openings and rearrangements.

AB - Kim's serendipitous synthesis of a novel cavitand by the one-pot reaction between phloroglucinol and ninhydrin was revisited and extended. A much deeper cavitand was obtained by replacing ninhydrin with benzo[f]ninhydrin. Performing the reaction in a stepwise manner, employing both ninhydrin and benzo[f]ninhydrin, provided 'mixed bowls' of lower symmetry. Other cyclic polyketones, such as 1,2-indanedione and alloxan, form with phloroglucinol only partially closed structures. Crystallographic studies of the intermediate compounds in this reaction confirm Kim's postulate that the bowl formation involves hemiketal ring-openings and rearrangements.

KW - Bowl-shaped compounds

KW - Hemiketals

KW - Ninhydrin

KW - Phloroglucinol

UR - https://www.scopus.com/pages/publications/68549092571

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DO - 10.1016/j.tet.2009.07.056

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SN - 0040-4020

VL - 65

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JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

The reaction between phloroglucinol and vic polycarbonyl compounds: extension and mechanistic elucidation of Kim's synthesis for bipolarofacial bowl-shaped compounds

Abstract

Keywords

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