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Synthesis of 2a,8b-Dihydrocyclobuta[a]naphthalene-3,4-diones
On irradiation (λ = 350 nm) in neat hex-1-yne, naphthalene-1,2-dione monoacetals 1 afford mixtures of pentacyclic photodimers and up to 25% (isolated yield) of mixed photocycloadducts 2. Careful acidic hydrolysis of the acetal function of 2 gives the title compounds 3, the overall sequence represent...
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| Formato: | Texto |
| Lenguaje: | English |
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Beilstein-Institut
2010
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2919270/ https://www.ncbi.nlm.nih.gov/pubmed/20703383 http://dx.doi.org/10.3762/bjoc.6.76 |
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| author | Schmidt, Kerstin Margaretha, Paul |
| author_facet | Schmidt, Kerstin Margaretha, Paul |
| author_sort | Schmidt, Kerstin |
| collection | PubMed |
| description | On irradiation (λ = 350 nm) in neat hex-1-yne, naphthalene-1,2-dione monoacetals 1 afford mixtures of pentacyclic photodimers and up to 25% (isolated yield) of mixed photocycloadducts 2. Careful acidic hydrolysis of the acetal function of 2 gives the title compounds 3, the overall sequence representing a first approach to a (formal) [2 + 2] photocycloadduct of a 1,2-naphthoquinone to an alkyne. |
| format | Text |
| id | pubmed-2919270 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2010 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-29192702010-08-11 Synthesis of 2a,8b-Dihydrocyclobuta[a]naphthalene-3,4-diones Schmidt, Kerstin Margaretha, Paul Beilstein J Org Chem Full Research Paper On irradiation (λ = 350 nm) in neat hex-1-yne, naphthalene-1,2-dione monoacetals 1 afford mixtures of pentacyclic photodimers and up to 25% (isolated yield) of mixed photocycloadducts 2. Careful acidic hydrolysis of the acetal function of 2 gives the title compounds 3, the overall sequence representing a first approach to a (formal) [2 + 2] photocycloadduct of a 1,2-naphthoquinone to an alkyne. Beilstein-Institut 2010-07-13 /pmc/articles/PMC2919270/ /pubmed/20703383 http://dx.doi.org/10.3762/bjoc.6.76 Text en Copyright © 2010, Schmidt and Margaretha 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 | Full Research Paper Schmidt, Kerstin Margaretha, Paul Synthesis of 2a,8b-Dihydrocyclobuta[a]naphthalene-3,4-diones |
| title | Synthesis of 2a,8b-Dihydrocyclobuta[a]naphthalene-3,4-diones |
| title_full | Synthesis of 2a,8b-Dihydrocyclobuta[a]naphthalene-3,4-diones |
| title_fullStr | Synthesis of 2a,8b-Dihydrocyclobuta[a]naphthalene-3,4-diones |
| title_full_unstemmed | Synthesis of 2a,8b-Dihydrocyclobuta[a]naphthalene-3,4-diones |
| title_short | Synthesis of 2a,8b-Dihydrocyclobuta[a]naphthalene-3,4-diones |
| title_sort | synthesis of 2a,8b-dihydrocyclobuta[a]naphthalene-3,4-diones |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2919270/ https://www.ncbi.nlm.nih.gov/pubmed/20703383 http://dx.doi.org/10.3762/bjoc.6.76 |
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