Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites
In this paper, we present a Lewis-acid-promoted reaction of 2-benzoylbenzaldehyde and trialkenyl phosphites, which resulted in the formation of polycyclic phosphonates. The reaction proceeded via nucleophilic attack of trialkenyl phosphite on the carbonyl carbon of 2-benzoylbenzaldehyde. The subsequ...
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De Gruyter
2019-05-01
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| Series: | Heterocyclic Communications |
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| Online Access: | https://doi.org/10.1515/hc-2019-0011 |
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doaj-d8656d92292247b4a4b8652b721dd7c52021-09-06T19:19:48ZengDe GruyterHeterocyclic Communications2191-01972019-05-01251737710.1515/hc-2019-0011Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphitesYamana Kenji0Nakano Hirofumi1Division of Liberal Arts and Sciences, Aichi Gakuin University, Araike 12, Iwasaki, Nisshin, Aichi 470-0195, JapanDepartment of Chemistry, Aichi University of Education, Igaya, Kariya, Aichi 448-8542, JapanIn this paper, we present a Lewis-acid-promoted reaction of 2-benzoylbenzaldehyde and trialkenyl phosphites, which resulted in the formation of polycyclic phosphonates. The reaction proceeded via nucleophilic attack of trialkenyl phosphite on the carbonyl carbon of 2-benzoylbenzaldehyde. The subsequent intramolecular Diels-Alder reaction led to the formation of the cyclic phosphonate.https://doi.org/10.1515/hc-2019-0011intramolecular cycloadditiondiels-alder reactionoxaphosphinaneisobenzofurancyclic phosphonate |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Yamana Kenji Nakano Hirofumi |
| spellingShingle |
Yamana Kenji Nakano Hirofumi Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites Heterocyclic Communications intramolecular cycloaddition diels-alder reaction oxaphosphinane isobenzofuran cyclic phosphonate |
| author_facet |
Yamana Kenji Nakano Hirofumi |
| author_sort |
Yamana Kenji |
| title |
Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites |
| title_short |
Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites |
| title_full |
Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites |
| title_fullStr |
Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites |
| title_full_unstemmed |
Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites |
| title_sort |
synthesis of polycyclic phosphonates via an intramolecular diels-alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites |
| publisher |
De Gruyter |
| series |
Heterocyclic Communications |
| issn |
2191-0197 |
| publishDate |
2019-05-01 |
| description |
In this paper, we present a Lewis-acid-promoted reaction of 2-benzoylbenzaldehyde and trialkenyl phosphites, which resulted in the formation of polycyclic phosphonates. The reaction proceeded via nucleophilic attack of trialkenyl phosphite on the carbonyl carbon of 2-benzoylbenzaldehyde. The subsequent intramolecular Diels-Alder reaction led to the formation of the cyclic phosphonate. |
| topic |
intramolecular cycloaddition diels-alder reaction oxaphosphinane isobenzofuran cyclic phosphonate |
| url |
https://doi.org/10.1515/hc-2019-0011 |
| work_keys_str_mv |
AT yamanakenji synthesisofpolycyclicphosphonatesviaanintramoleculardielsalderreactionof2benzoylbenzalaldehydeandalkenylphosphites AT nakanohirofumi synthesisofpolycyclicphosphonatesviaanintramoleculardielsalderreactionof2benzoylbenzalaldehydeandalkenylphosphites |
| _version_ |
1717777777838522368 |