- 作者: An-Tai Wu, Wen-Dar Liu and Wen-Sheng Chung*
- 作者服務機構: Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan 30050, R.O.C.
- 中文摘要: 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.
- 英文摘要: --
- 中文關鍵字: Naphthosultine; Benzodisultine; Pyrolysis; Diels-Alder reaction; o-Quinodimethanes; Tetramethylenebenzene.
- 英文關鍵字: Naphthosultine; Benzodisultine; Pyrolysis; Diels-Alder reaction; o-Quinodimethanes; Tetramethylenebenzene.