Browsing by Author "Chuang, CT"

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Intramolecular Diels-Alder reaction of furans with allenyl ethers followed by phenylthio and trialkylsilyl groups rearrangement
(1998-12-01)
Chuang, CT
;
Yen, CH
;
Wu, HJ
;
應用化學系
;
Department of Applied Chemistry
a new reaction involving an intramolecular Diels-Alder reaction of a furan diene with an allenyl ether dienophile followed by phenylthio group rearrangement was discovered. Treatment of the propargyl ethers 2a-c with t-BuOK in t-BuOH at 85 degrees C gave the phenylthio group rearrangement products 5a-c and 6a-c. A reaction involving an intramolecular Diels-Alder reaction of a furan diene with an allenyl ether dienophile followed by trialkylsilyl group rearrangement is also demonstrated.
Intramolecular Diels-Alder reaction of furans with allenyl ethers followed by phenylthio and trialkylsilyl groups rearrangement
(1998-12-01)
Chuang, CT
;
Yen, CH
;
Wu, HJ
;
應用化學系
;
Department of Applied Chemistry
a new reaction involving an intramolecular Diels-Alder reaction of a furan diene with an allenyl ether dienophile followed by phenylthio group rearrangement was discovered. Treatment of the propargyl ethers 2a-c with t-BuOK in t-BuOH at 85 degrees C gave the phenylthio group rearrangement products 5a-c and 6a-c. A reaction involving an intramolecular Diels-Alder reaction of a furan diene with an allenyl ether dienophile followed by trialkylsilyl group rearrangement is also demonstrated.
Intramolecular Diels-Alder reaction of furans with allenyl ethers followed by sulfur and silicon atom-containing group rearrangement
(1998-07-24)
Wu, HJ
;
Yen, CH
;
Chuang, CT
;
應用化學系
;
Department of Applied Chemistry
The intramolecular Diels-Alder reactions of a furandiene with an allenyl ether dienophile followed by the alkylthio, alkylsulfinyl, alkylsulfonyl, and trimethylsilyl group rearrangements are reported. Refluxing the propargyl ether 3 with t-BuOK in t-BuOH at 85 degrees C gave the 1,4-rearrangement product 4 exclusively. The alkylthio group 1,4-rearrangement may proceed intramolecularly via the tight; ion pairs. Refluxing the 5-(alkylsulfinyl)-2-furfuryl propargyl ethers 9a-e and the 5-(alkylsulfonyl)-2-furfuryl propargyl ethers 19a-e under the same reaction conditions gave the alkylsulfinyl group and the alkylsulfonyl group 1,2-rearrangement products 10a-e and 20a-e, respectively. No detectable amount of the corresponding 1,4-rearrangement products 11a-e and 21a-e was obtained. In the cases of 9b and 19b, which possess two furfurylic hydrogen atoms, no detectable amount of the furan ring-transfer reaction products was obtained. Refluxing the 5-(trimethylsilyl)-2-furfuryl propargyl ethers 25a-d with t-BuOK in t-BuOH at 85 degrees C for 10 h gave the trimethylsilyl group 1,2-rearrangement products 26a-d and Brook rearrangement products 27a-d. The reaction mechanisms for these novel intramolecular Diels-Alder reactions are discussed. In the case of 37, which possesses two furfurylic hydrogen atoms, compound 38 was obtained via an intramolecular Diels-Alder reaction followed by the furan ring-transfer reaction and Brook rearrangement.
Intramolecular Diels-Alder reaction of furans with allenyl ethers followed by trimethylsilyl group 1,2-rearrangement and Brook rearrangement
(1996-10-07)
Wu, HJ
;
Yen, CH
;
Chuang, CT
;
應用化學系
;
Department of Applied Chemistry
The base-catalyzed intramolecular Diels-Alder reactions of 5-trimethylsilyl-2-furfuryl propargyl ethers la-lf gave compounds 2a-2f and 3a-3f in 70-90% yields respectively, a novel reaction involving an intramolecular Diels-Alder reaction followed by a trimethylsilyl group 1,2-rearrangement and Brook rearrangement. Copyright (C) 1996 Elsevier Science Ltd
Intramolecular Diels-Alder reaction of furans with allenyl ethers followed by trimethylsilyl group 1,2-rearrangement and Brook rearrangement
(1996-10-07)
Wu, HJ
;
Yen, CH
;
Chuang, CT
;
交大名義發表
;
應用化學系
The base-catalyzed intramolecular Diels-Alder reactions of 5-trimethylsilyl-2-furfuryl propargyl ethers la-lf gave compounds 2a-2f and 3a-3f in 70-90% yields respectively, a novel reaction involving an intramolecular Diels-Alder reaction followed by a trimethylsilyl group 1,2-rearrangement and Brook rearrangement. Copyright (C) 1996 Elsevier Science Ltd