2005
DOI: 10.1070/mc2005v015n02abeh002072
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4,5-Difluoro-1,2-dehydrobenzene: generation and cycloaddition reactions

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Cited by 15 publications
(9 citation statements)
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“…The key building block 5,6‐difluoro‐1 H ‐benzotriazole was readily prepared in 75% yield from 5,6‐difluorobenzene‐1,2‐diamine by treatment with sodium nitrite. [ 47 ] Alkylation with the appropriate bromoalkane using Cs 2 CO 3 in dimethylformamide afforded a mixture of the desired product 2‐alkyl‐5,6‐difluorobenzotriazole (dfBTz) and the isomeric 1‐alkyl‐5,6‐difluorobenzotriazole, which required separation by column chromatography. The synthesis of alkylating agents is shown in Scheme S1 (Supporting Information), but we highlight that 11‐(bromomethyl)tricosane (to give 2DT) was readily prepared in one step from the commercial alcohol, whereas 11‐(4‐bromobutyl)tricosane (to give 5DH) required a four‐step synthesis.…”
Section: Resultsmentioning
confidence: 99%
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“…The key building block 5,6‐difluoro‐1 H ‐benzotriazole was readily prepared in 75% yield from 5,6‐difluorobenzene‐1,2‐diamine by treatment with sodium nitrite. [ 47 ] Alkylation with the appropriate bromoalkane using Cs 2 CO 3 in dimethylformamide afforded a mixture of the desired product 2‐alkyl‐5,6‐difluorobenzotriazole (dfBTz) and the isomeric 1‐alkyl‐5,6‐difluorobenzotriazole, which required separation by column chromatography. The synthesis of alkylating agents is shown in Scheme S1 (Supporting Information), but we highlight that 11‐(bromomethyl)tricosane (to give 2DT) was readily prepared in one step from the commercial alcohol, whereas 11‐(4‐bromobutyl)tricosane (to give 5DH) required a four‐step synthesis.…”
Section: Resultsmentioning
confidence: 99%
“…The key building block 5,6-difluoro-1H-benzotriazole was readily prepared in 75% yield from 5,6-difluorobenzene-1,2-diamine by treatment with sodium nitrite. [47] Alkylation with the appropriate bromoalkane using Cs 2 CO 3 in dimethylformamide afforded a mixture of the desired product 2-alkyl-5,6-difluorobenzotriazole (dfBTz) Scheme 1. Synthesis of target polymers.…”
Section: Polymer Design and Synthesismentioning
confidence: 99%
“…The reaction was complete after 4 h. Purification by silica gel flash column chromatography eluting with 30 % ethyl acetate in hexane gave 5,6‐difluoro‐1 H ‐benzo[ d ][1.2.3]triazole ( 2k ) (0.0950 g, 61 %) as an off‐white solid. Mp 176–178 °C (lit . 183–184 °C).…”
Section: Methodsmentioning
confidence: 99%
“…The intermediates and monomers (BTz, BTz-F, BTz-OR) were prepared by modifying the previously reported procedures [15][16][17][18][19][20][21]. 1 H and 13 C NMR spectra were recorded on a JEOL (JNM-AL300) FT NMR system operating at 300 and 75 MHz, respectively.…”
Section: Experimental Section Materialsmentioning
confidence: 99%