Dimerization and comments on the reactivity of homophthalic anhydride()

Homophthalic anhydride (HPA) dimerizes under the influence of base to provide, sequentially, the (3-4’)-C-acyl dimer, a pair of chiral diastereomeric bis(lactones), 3-(2-carboxybenzyl)isocoumarin-4-carboxylic acid, and finally, 3-(2-carboxybenzyl)isocoumarin. The structures of the bis(lactones) were...

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Publicado no:Tetrahedron Lett
Main Authors: Hong, Julia, Wang, Zheng, Levin, Aaron, Emge, Thomas J., Floyd, David M., Knapp, Spencer
Formato: Artigo
Idioma:Inglês
Publicado em: 2014
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Article
Acesso em linha:https://ncbi.nlm.nih.gov/pmc/articles/PMC4481714/
https://ncbi.nlm.nih.gov/pubmed/26124537
https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1016/j.tetlet.2014.10.027
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spelling pubmed-44817142016-06-03 Dimerization and comments on the reactivity of homophthalic anhydride() Hong, Julia Wang, Zheng Levin, Aaron Emge, Thomas J. Floyd, David M. Knapp, Spencer Tetrahedron Lett Article Homophthalic anhydride (HPA) dimerizes under the influence of base to provide, sequentially, the (3-4’)-C-acyl dimer, a pair of chiral diastereomeric bis(lactones), 3-(2-carboxybenzyl)isocoumarin-4-carboxylic acid, and finally, 3-(2-carboxybenzyl)isocoumarin. The structures of the bis(lactones) were misassigned in 1970 based on the (presumed) cis thermal decarboxylative elimination reaction of the lower melting one. The preferred pathway should be trans-anti, however, and crystallographic analysis of one of the bis(lactones) reverses the earlier assignment. The formal cycloaddition reaction of HPA with imines occurs in preference to HPA dimerization; the mechanistic implications of this reactivity difference are discussed. 2014-09-12 2015-06-03 /pmc/articles/PMC4481714/ /pubmed/26124537 http://dx.doi.org/10.1016/j.tetlet.2014.10.027 Text en © 2014 Elsevier Ltd. All rights reserved.
institution US NLM
collection PubMed Central
language Inglês
format Artigo
topic Article
spellingShingle Article
Hong, Julia
Wang, Zheng
Levin, Aaron
Emge, Thomas J.
Floyd, David M.
Knapp, Spencer
Dimerization and comments on the reactivity of homophthalic anhydride()
description Homophthalic anhydride (HPA) dimerizes under the influence of base to provide, sequentially, the (3-4’)-C-acyl dimer, a pair of chiral diastereomeric bis(lactones), 3-(2-carboxybenzyl)isocoumarin-4-carboxylic acid, and finally, 3-(2-carboxybenzyl)isocoumarin. The structures of the bis(lactones) were misassigned in 1970 based on the (presumed) cis thermal decarboxylative elimination reaction of the lower melting one. The preferred pathway should be trans-anti, however, and crystallographic analysis of one of the bis(lactones) reverses the earlier assignment. The formal cycloaddition reaction of HPA with imines occurs in preference to HPA dimerization; the mechanistic implications of this reactivity difference are discussed.
author Hong, Julia
Wang, Zheng
Levin, Aaron
Emge, Thomas J.
Floyd, David M.
Knapp, Spencer
author_facet Hong, Julia
Wang, Zheng
Levin, Aaron
Emge, Thomas J.
Floyd, David M.
Knapp, Spencer
author_sort Hong, Julia
title Dimerization and comments on the reactivity of homophthalic anhydride()
title_short Dimerization and comments on the reactivity of homophthalic anhydride()
title_full Dimerization and comments on the reactivity of homophthalic anhydride()
title_fullStr Dimerization and comments on the reactivity of homophthalic anhydride()
title_full_unstemmed Dimerization and comments on the reactivity of homophthalic anhydride()
title_sort dimerization and comments on the reactivity of homophthalic anhydride()
container_title Tetrahedron Lett
publishDate 2014
url https://ncbi.nlm.nih.gov/pmc/articles/PMC4481714/
https://ncbi.nlm.nih.gov/pubmed/26124537
https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1016/j.tetlet.2014.10.027
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