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http://ir.ncue.edu.tw/ir/handle/987654321/15023
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| Title: | The Synthesis of Naphthosultine and Benzodisultines and Their Py Rolysis with Dienophiles: Studies on o-Naphthoquinodimethane and Bis-o-Quinodimethane |
| Authors: | Wu, An-Tai;Liu, Wen-Dar;Chung, Wen-Sheng |
| Contributors: | 化學系 |
| Date: | 2002-02
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| Issue Date: | 2013-01-07T01:47:32Z
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| Publisher: | 中國化學學會 |
| Abstract: | Sealed tube reactions of the naphthosultine 8 with a series of electron-deficient dienophiles (fumaro - nitrile, N-phenylmaleimide, dimethyl fumarate, and dimethyl acetylenedicarboxylate) intoluene 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 (so dium form aldehyde 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 thermalextrusion of sulfur dioxide from these sultines led to ei ther o-naphthoquinodimethane 6 (from 8) or bis-o-quinodimethane 19 (from 17 and 18); subsequent trapping of these reactive in termediates by dienophiles and SO2 gave various 1:1 and 1:2 Diels-Alder adducts in modest to excellent yields. |
| Relation: | J. Chin. Chem. Soc., 49(1): 77-82 |
| Appears in Collections: | [化學系] 期刊論文
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