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題名 | The Synthesis of Naphthosultine and Benzodisultines and their Pyrolysis with Dienophiles: Studies on o-Naphthoquinodimethane and Bis-o-quinodimethane= |
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作者 | 吳安台; 劉文達; 鍾文聖; Wu, An-tai; Liu, Wen-dar; Chung, Wen-sheng; |
期刊 | Journal of the Chinese Chemical Society |
出版日期 | 20020200 |
卷期 | 49:1 2002.02[民91.02] |
頁次 | 頁77-82 |
分類號 | 346.01 |
語文 | eng |
關鍵詞 | Naphthosultine; Benzodisultine; Pyrolysis; Diels-Alder reaction; o-Quinodimethanes; Tetramethylenebenzene; |
英文摘要 | Sealed tube reactions of the naphthosultine 8 with a series of electron-deficient dienophiles (fumaronitrile, N-phenylmaleimide, dimethyl fumarate, and dimethyl acetylenedicarboxylate) in toluene at 180 °C gave corresponding 1:1 cycloadducts 11-14 in various amounts along with rearranged naphthosulfolene 7 in 67-95% yields. The reaction of 1,2,4,5-tetra(bromomethyl)benzene with Rongalite (sodium formaldehyde sulfoxylate) and tetrabutylammonium bromide in DMF gave benzodisultines 17 and 18 in a combined yield of 56%. Sealed tube reactions of benzodisultines 17 and 18 with a series of dienophiles in xylene at 200 °C gave corresponding 1:1 and 1:2 cycloadducts 20-27. The results suggested that thermal extrusion of sulfur dioxide from these sultines led to either o-naphthoquinodimethane 6 (from 8) or bis-o-quinodimethane 19 (from 17 and 18); subsequent trapping of these reactive intermediates by dienophiles and SO2 gave various 1:1 and 1:2 Diels-Alder adducts in modest to excellent yields. |
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