Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran

The reaction of di-(o-acetylphenyl)acetylene (1) with excess dimethyl acetylenedicarboxylate (DMAD) produced bis-DMAD adducts meso-3 and rac-3. This transformation is suggested to involve thermal rearrangement of 1 to the intermediate 3,3'-dimethyl-1,1'-biisobenzofuran (A), and subsequent...

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Detalles Bibliográficos
Autores principales: Casey, Charles P, Strotman, Neil A, Guzei, Ilia A
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2005
Materias:
Preliminary Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399466/
https://www.ncbi.nlm.nih.gov/pubmed/16542028
http://dx.doi.org/10.1186/1860-5397-1-18
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author Casey, Charles P
Strotman, Neil A
Guzei, Ilia A
author_facet Casey, Charles P
Strotman, Neil A
Guzei, Ilia A
author_sort Casey, Charles P
collection PubMed
description The reaction of di-(o-acetylphenyl)acetylene (1) with excess dimethyl acetylenedicarboxylate (DMAD) produced bis-DMAD adducts meso-3 and rac-3. This transformation is suggested to involve thermal rearrangement of 1 to the intermediate 3,3'-dimethyl-1,1'-biisobenzofuran (A), and subsequent Diels-Alder cycloadditions of two equivalents of DMAD to A. The isolation of trapping products meso-3 and rac-3, which contain complex polycyclic frameworks, provide strong evidence for the transient production of A, the first biisobenzofuran. An X-ray crystal structure of meso-3 was obtained.
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spelling pubmed-13994662006-03-13 Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran Casey, Charles P Strotman, Neil A Guzei, Ilia A Beilstein J Org Chem Preliminary Communication The reaction of di-(o-acetylphenyl)acetylene (1) with excess dimethyl acetylenedicarboxylate (DMAD) produced bis-DMAD adducts meso-3 and rac-3. This transformation is suggested to involve thermal rearrangement of 1 to the intermediate 3,3'-dimethyl-1,1'-biisobenzofuran (A), and subsequent Diels-Alder cycloadditions of two equivalents of DMAD to A. The isolation of trapping products meso-3 and rac-3, which contain complex polycyclic frameworks, provide strong evidence for the transient production of A, the first biisobenzofuran. An X-ray crystal structure of meso-3 was obtained. Beilstein-Institut 2005-12-09 /pmc/articles/PMC1399466/ /pubmed/16542028 http://dx.doi.org/10.1186/1860-5397-1-18 Text en Copyright © 2005, Casey et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Preliminary Communication
Casey, Charles P
Strotman, Neil A
Guzei, Ilia A
Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran
title Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran
title_full Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran
title_fullStr Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran
title_full_unstemmed Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran
title_short Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran
title_sort trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran
topic Preliminary Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399466/
https://www.ncbi.nlm.nih.gov/pubmed/16542028
http://dx.doi.org/10.1186/1860-5397-1-18
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AT guzeiiliaa trappingevidenceforthethermalcyclizationofdioacetylphenylacetyleneto33dimethyl11biisobenzofuran

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