Browsing by Author "Lin, Chu-Chung"

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3-Formylpyrroles from 3-Furfurylamines by Bromine Oxidation Reaction
(2010-12-01)
Harn, Piin-Jye
;
Lin, Chu-Chung
;
Wu, Hsien-Jen
;
應用化學系
;
Department of Applied Chemistry
Oxidation of 3-furfurylamines 3a-e with bromine in acetone-water solution gave N-substituted 3-formylpyrroles 4a-e in good yields. A reaction mechanism via the Clauson-Kaas reaction followed by the cis-trans isomerization of the 2-ene-1,4-diones 13 and 14 was proposed to account for the formation of the pyrroles 4a-e.
Exploring a sulfone linker utilizing trimethyl aluminum as a cleavage reagent: solid-phase synthesis of sulfonamides and ureas
(2012-08-01)
Chung, Tsai-Wen
;
Chen, Chih-Hau
;
Lin, Chu-Chung
;
Wu, Hsien-Jen
;
Sun, Chung-Ming
A novel and efficient cleavage reagent, trimethyl aluminum, for traceless sulfinate-functionalized resin has been developed. The synthesis of sulfonamide and urea derivatives via a traceless solid-phase sulfone linker strategy through six synthetic steps comprising utilization of trimethyl aluminum as a novel cleavage reagent was also established. An insight of the plausible mechanism of the cleavage reaction was discussed.
Oxidation of 3-furfurylcarbinois with bromine in acetone-water
(2008-02-01)
Harn, Piin-Jye
;
Lin, Chu-Chung
;
Wu, Hsien-Jen
;
應用化學系
;
Department of Applied Chemistry
Oxidation of 3-furfurylcarbinols 3a-e and 7 with bromine in acetone-water solution gave the 2-substituted-3-furfurals 4a-e and 8 in good yields, respectively. Reaction of 2-alkyl-3-furfurylcarbinols 9a and 9b with bromine in acetone-water gave the bromoalkyl 3-furfuryl ketones 10a and 10b as the major products. A reaction mechanism via the cis-trans isomerization of the 2-ene-1,4-diones 13 and 14 was proposed to account for the transposition of the alkyl group of the 3-furfurylcarbinols 3, 7 and 9 to the 2-position on the furan ring of the products 4, 8 and 10.
Ozonolysis of bis-endo-diacylbicyclo[2.2.1]heptenes in dichloromethane-methanol
(2011-09-23)
Lin, Hui-Chang
;
Lin, Chu-Chung
;
Wu, Hsien-Jen
;
應用化學系
;
Department of Applied Chemistry
Ozonolysis of bis-endo-diacylbicyclo[2.2.1]heptenes 3a-d at -78 degrees C in dichloromethane methanol gave the hydroperoxides 6a-d in 70-80% yields. Ozonolysis of bis-endo-diacetylbicyclo[2.2.2]octene 15 and bis-endo-diacetyl-7-oxabicyclo-[2.2.1]heptene 16 under the same reaction conditions gave the hydroperoxides 17 and 18, respectively. The intramolecular sequential nucleophilic addition of the carbonyl groups to the carbonyl oxide group was observed for the first time and was found to be faster than the intermolecular nucleophilic addition of a methanol molecule to the carbonyl oxide group. Ozonolysis of compound 23 in CH(2)Cl(2)-MeOH at -78 degrees C followed by reduction with Me(2)S gave compounds 24 and 25, in which the stereochemistry of the methoxyl groups was determined by X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.