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New Anthracenyl-Substituted Phosphonates: Synthesis and Utility
| Content Provider | Scilit |
|---|---|
| Author | Srinivas, Venu |
| Editor | Swamy, K. Kumara Kumar, K. Pavan |
| Copyright Year | 2007 |
| Description | Chlorination of α-hydroxyphosphonate $anthracen-9-yl(5,5-dimethyl-2-oxo-2λ^{5}$-1,3,2-dioxaphosphinan-2-yl)methanol (11) using thionyl chloride unexpectedly yields $10-(5,5-dimethyl-2-oxo-2λ^{5}$-1,3,2-dioxaphosphinan-2-ylmethylene)anthracen-9(10H)-one (13), $2-(10-chloroanthracen-9-ylmethyl)-5,5-dimethyl-2λ^{5}$-1,3,2-dioxaphosphinan-2-one (14), and $10-(5,5-dimethyl-2-oxo-2λ^{5}$-1,3,2-dioxaphosphinan-2-ylmethylene)-9,10-dihydroanthracen-9-ol (15) in addition to $2-[anthracen-9-yl(chloro)methyl]-5,5-dimethyl-2λ^{5}$-1,3,2-dioxaphosphinan-2-one (12). The reaction of 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphinane (5) with 9-anthraldehyde leads to 2-chloro-1,1-dimethylethyl hydrogen $10-(5,5-dimethyl-2-oxo-2λ^{5}$-1,3,2-dioxaphosphinan-2-ylmethylene)-4a,9,9a,10-tetrahydroanthracen-9-ylphosphonate (20) in addition to 12. Bromination of 11 with phosphorus tribromide affords the 10-bromoanthracen-9-yl product, $2-(10-bromoanthracen-9-ylmethyl)-5,5-dimethyl-2λ^{5}$-1,3,2-dioxaphosphinan-2-one (22). Reaction of 12 with 4-chloro- or 4-nitrobenzaldehyde in the presence of sodium hydride affords the products, 9-(2-arylvinyl)anthracenes 23 and 24 in an uncommon Horner-Wadsworth-Emmons-type reaction. Compound 22 underwent the normal Horner-Wadsworth-Emmons reaction with benzaldehydes or ferrocenecarbaldehyde to afford disubstituted alkenes. One of these alkenes, (E)-9-bromo-10-[2-(4-bromophenyl)vinyl]anthracene (26), undergoes Sonogashira coupling with terminal alkynes to afford the conjugated alkynes (E)-9-bromo-10-[2-(4-ethynylphenyl)vinyl]anthracenes 30-32 in moderate yields. X-ray crystal structures of 12-15, 20, 23 and (E)-9-bromo-10-[2-(4-methoxyphenyl)vinyl]anthracene (27) have been determined. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2007-965947.pdf |
| Ending Page | 901 |
| Page Count | 9 |
| Starting Page | 893 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-2007-965947 |
| Journal | Synthesis |
| Issue Number | 6 |
| Volume Number | 2007 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2007-02-20 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry Horner-wadsworth-emmons Reaction |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
