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Please use this identifier to cite or link to this item: http://ir.ncue.edu.tw/ir/handle/987654321/15023

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
Issue Date: 2013-01-07T01:47:32Z
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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