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N,N-Dimethylformamide Dimethylacetal (DMF-DMA) Catalyzed Formation of 1,3,5- Trisubstituted Benzene Derivatives from α,β-Unsaturated Nitro Compounds
| Content Provider | Semantic Scholar |
|---|---|
| Author | Kim, Hyoung Shik Lee, Ka Young Kim, Jae Nyoung |
| Copyright Year | 1999 |
| Abstract | C within20 h as shown in Scheme 1. Some variations in reaction con-ditions such as temperature, amounts of DMF-DMA, orreaction time did not improve the yield of 2a. Substituted β-nitrostyrene derivatives 1b-c or heterocyclicderivatives 1d-e afforded the corresponding compounds 2b-e in 20-40% yields. However, alkyl derivative 1f or β-substi-tuted nitro olefin 1g did not give the desired products. Themechanism for the formation of 1,3,5-triarylbenzenes 2a-ecan be proposed as shown in Scheme 2. Addition of methox-ide ion to β-nitrostyrene gave a new nucleophilic intermedi-ate I, which adds to β-nitrostyrene to give II, same reactiononce again, cyclization, elimination of nitrous acid afford thedesired product. |
| File Format | PDF HTM / HTML |
| DOI | 10.1002/chin.200016096 |
| Alternate Webpage(s) | http://ocean.kisti.re.kr/downfile/volume/chemical/JCGMCS/1999/v20n11/JCGMCS_1999_v20n11_1255.pdf |
| Alternate Webpage(s) | https://doi.org/10.1002/chin.200016096 |
| Volume Number | 31 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |