TY - JOUR
T1 - The reaction between phloroglucinol and vic polycarbonyl compounds
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 - http://www.scopus.com/inward/record.url?scp=68549092571&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2009.07.056
DO - 10.1016/j.tet.2009.07.056
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AN - SCOPUS:68549092571
SN - 0040-4020
VL - 65
SP - 7954
EP - 7962
JO - Tetrahedron
JF - Tetrahedron
IS - 38
ER -